{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,3,9]],"date-time":"2026-03-09T08:58:16Z","timestamp":1773046696742,"version":"3.50.1"},"reference-count":81,"publisher":"MDPI AG","issue":"1","license":[{"start":{"date-parts":[[2022,12,27]],"date-time":"2022-12-27T00:00:00Z","timestamp":1672099200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100004281","name":"Narodowe Centrum Nauki","doi-asserted-by":"publisher","award":["2019\/35\/D\/ST4\/00806"],"award-info":[{"award-number":["2019\/35\/D\/ST4\/00806"]}],"id":[{"id":"10.13039\/501100004281","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100004281","name":"Narodowe Centrum Nauki","doi-asserted-by":"publisher","award":["CAREER CHE-1650766"],"award-info":[{"award-number":["CAREER CHE-1650766"]}],"id":[{"id":"10.13039\/501100004281","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100004281","name":"Narodowe Centrum Nauki","doi-asserted-by":"publisher","award":["2022YFF0710402"],"award-info":[{"award-number":["2022YFF0710402"]}],"id":[{"id":"10.13039\/501100004281","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100000001","name":"Rutgers University and the NSF","doi-asserted-by":"publisher","award":["2019\/35\/D\/ST4\/00806"],"award-info":[{"award-number":["2019\/35\/D\/ST4\/00806"]}],"id":[{"id":"10.13039\/100000001","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100000001","name":"Rutgers University and the NSF","doi-asserted-by":"publisher","award":["CAREER CHE-1650766"],"award-info":[{"award-number":["CAREER CHE-1650766"]}],"id":[{"id":"10.13039\/100000001","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100000001","name":"Rutgers University and the NSF","doi-asserted-by":"publisher","award":["2022YFF0710402"],"award-info":[{"award-number":["2022YFF0710402"]}],"id":[{"id":"10.13039\/100000001","id-type":"DOI","asserted-by":"publisher"}]},{"name":"national key research and development program of China","award":["2019\/35\/D\/ST4\/00806"],"award-info":[{"award-number":["2019\/35\/D\/ST4\/00806"]}]},{"name":"national key research and development program of China","award":["CAREER CHE-1650766"],"award-info":[{"award-number":["CAREER CHE-1650766"]}]},{"name":"national key research and development program of China","award":["2022YFF0710402"],"award-info":[{"award-number":["2022YFF0710402"]}]},{"name":"2115 Talent Development Program of China Agricultural University","award":["2019\/35\/D\/ST4\/00806"],"award-info":[{"award-number":["2019\/35\/D\/ST4\/00806"]}]},{"name":"2115 Talent Development Program of China Agricultural University","award":["CAREER CHE-1650766"],"award-info":[{"award-number":["CAREER CHE-1650766"]}]},{"name":"2115 Talent Development Program of China Agricultural University","award":["2022YFF0710402"],"award-info":[{"award-number":["2022YFF0710402"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Benzylic alcohols are among the most important intermediates in organic synthesis. Recently, the use of abundant metals has attracted significant attention due to the issues with the scarcity of platinum group metals. Herein, we report a sequential method for the synthesis of benzylic alcohols by a merger of iron catalyzed cross-coupling and highly chemoselective reduction of benzamides promoted by sodium dispersion in the presence of alcoholic donors. The method has been further extended to the synthesis of deuterated benzylic alcohols. The iron-catalyzed Kumada cross-coupling exploits the high stability of benzamide bonds, enabling challenging C(sp2)\u2013C(sp3) cross-coupling with alkyl Grignard reagents that are prone to dimerization and \u03b2-hydride elimination. The subsequent sodium dispersion promoted reduction of carboxamides proceeds with full chemoselectivity for the C\u2013N bond cleavage of the carbinolamine intermediate. The method provides access to valuable benzylic alcohols, including deuterium-labelled benzylic alcohols, which are widely used as synthetic intermediates and pharmacokinetic probes in organic synthesis and medicinal chemistry. The combination of two benign metals by complementary reaction mechanisms enables to exploit underexplored avenues for organic synthesis.<\/jats:p>","DOI":"10.3390\/molecules28010223","type":"journal-article","created":{"date-parts":[[2022,12,27]],"date-time":"2022-12-27T03:03:31Z","timestamp":1672110211000},"page":"223","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":3,"title":["Sequential Iron-Catalyzed C(sp2)\u2013C(sp3) Cross-Coupling of Chlorobenzamides\/Chemoselective Amide Reduction and Reductive Deuteration to Benzylic Alcohols"],"prefix":"10.3390","volume":"28","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-7070-2468","authenticated-orcid":false,"given":"Elwira","family":"Bisz","sequence":"first","affiliation":[{"name":"Department of Chemistry, Opole University, 48 Oleska Street, 45-052 Opole, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Pamela","family":"Podchorodecka","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Opole University, 48 Oleska Street, 45-052 Opole, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Hengzhao","family":"Li","sequence":"additional","affiliation":[{"name":"Department of Nutrition and Health, China Agricultural University, Beijing 100193, China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Wioletta","family":"Och\u0119dzan-Siod\u0142ak","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Opole University, 48 Oleska Street, 45-052 Opole, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1521-009X","authenticated-orcid":false,"given":"Jie","family":"An","sequence":"additional","affiliation":[{"name":"Department of Nutrition and Health, China Agricultural University, Beijing 100193, China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9650-9690","authenticated-orcid":false,"given":"Michal","family":"Szostak","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Rutgers University, 73 Warren Street, Newark, NJ 07102, USA"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2022,12,27]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"624","DOI":"10.1246\/cl.2005.624","article-title":"Advances in Iron Catalyzed Cross Coupling Reactions","volume":"34","author":"Martin","year":"2005","journal-title":"Chem. Lett."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"1500","DOI":"10.1021\/ar800039x","article-title":"The Promise and Challenge of Iron-Catalyzed Cross Coupling","volume":"41","author":"Sherry","year":"2008","journal-title":"Acc. Chem. Res."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"396","DOI":"10.1002\/cssc.200900055","article-title":"Coming of Age: Sustainable Iron-Catalyzed Cross-Coupling Reactions","volume":"2","author":"Czaplik","year":"2009","journal-title":"ChemSusChem"},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"3170","DOI":"10.1021\/cr500425u","article-title":"Iron Catalysis in Organic Synthesis","volume":"115","author":"Bauer","year":"2015","journal-title":"Chem. Rev."},{"key":"ref_5","unstructured":"Marek, I., and Rappoport, Z. (2014). The Chemistry of Organoiron Compounds, Wiley."},{"key":"ref_6","doi-asserted-by":"crossref","unstructured":"Plietker, B. (2011). Iron Catalysis\u2014Fundamentals and Applications, Springer.","DOI":"10.1007\/978-3-642-14670-1"},{"key":"ref_7","doi-asserted-by":"crossref","unstructured":"Bauer, E.B. (2015). Iron Catalysis II, Springer.","DOI":"10.1007\/978-3-319-19396-0"},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"1","DOI":"10.15227\/orgsyn.096.0001","article-title":"Discussion Addendum for: 4-Nonylbenzoic Acid","volume":"96","year":"2019","journal-title":"Org. Synth."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"1541","DOI":"10.1039\/C5NP00059A","article-title":"Iron-promoted C-C bond formation in the total synthesis of natural products and drugs","volume":"32","author":"Legros","year":"2015","journal-title":"Nat. Prod. Rep."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"3964","DOI":"10.1002\/cssc.201701287","article-title":"Iron-Catalyzed C-O Bond Activation: Opportunity for Sustainable Catalysis","volume":"10","author":"Bisz","year":"2017","journal-title":"ChemSusChem"},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"778","DOI":"10.1021\/acscentsci.6b00272","article-title":"Iron Catalysis in Organic Synthesis: A Critical Assessment of What It Takes To Make This Base Metal a Multitasking Champion","volume":"2","year":"2016","journal-title":"ACS Cent. Sci."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"2362","DOI":"10.1002\/adsc.201600729","article-title":"Base-Metal Catalysis Marries Utilitarian Aspects with Academic Fascination","volume":"358","year":"2016","journal-title":"Adv. Synth. Catal."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"313","DOI":"10.1016\/j.chempr.2017.02.014","article-title":"Catalyst: Sustainable Catalysis","volume":"2","author":"Ludwig","year":"2017","journal-title":"Chem"},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"8493","DOI":"10.1021\/acscatal.1c00928","article-title":"Additive and Counterion Effects in Iron-Catalyzed Reactions Relevant to C-C Bond Formation","volume":"11","author":"Bakas","year":"2021","journal-title":"ACS Catal."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"e202114986","DOI":"10.1002\/anie.202114986","article-title":"A TMEDA\u2013Iron Adduct Reaction Manifold in Iron-Catalyzed C(sp2)\u2212C(sp3) Cross-Coupling Reactions","volume":"61","author":"Bakas","year":"2022","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"2461","DOI":"10.1021\/acs.oprd.1c00235","article-title":"Air-Stable Iron-Based Precatalysts for Suzuki\u2013Miyaura Cross-Coupling Reactions between Alkyl Halides and Aryl Boronic Esters","volume":"25","author":"Wong","year":"2021","journal-title":"Org. Process Res. Dev."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"5958","DOI":"10.1021\/acs.orglett.1c02053","article-title":"Dilithium Amides as a Modular Bis-Anionic Ligand Platform for Iron-Catalyzed Cross-Coupling","volume":"23","author":"Zhang","year":"2021","journal-title":"Org. Lett."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"140","DOI":"10.1021\/acs.accounts.8b00519","article-title":"Development and Evolution of Mechanistic Understanding in Iron-Catalyzed Cross-Coupling","volume":"52","author":"Neidig","year":"2019","journal-title":"Acc. Chem. Res."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"5392","DOI":"10.1002\/anie.201914315","article-title":"Rational Design of an Iron-Based Catalyst for Suzuki\u2013Miyaura Cross-Couplings Involving Heteroaromatic Boronic Esters and Tertiary Alkyl Electrophiles","volume":"59","author":"Crockett","year":"2020","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"1485","DOI":"10.1021\/acs.accounts.5b00042","article-title":"How Low Does Iron Go? Chasing the Active Species in Fe-Catalyzed Cross-Coupling Reactions","volume":"48","author":"Bedford","year":"2015","journal-title":"Acc. Chem. Res."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"1640","DOI":"10.1021\/acscatal.5b02441","article-title":"Active Species and Mechanistic Pathways in Iron-Catalyzed C\u2013C Bond-Forming Cross-Coupling Reactions","volume":"6","author":"Cassani","year":"2016","journal-title":"ACS Catal."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"6496","DOI":"10.1002\/anie.201802087","article-title":"The N-Methylpyrrolidone (NMP) Effect in Iron-Catalyzed Cross-Coupling with Simple Ferric Salts and MeMgBr","volume":"57","author":"Daifuku","year":"2018","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"2769","DOI":"10.1002\/anie.201813578","article-title":"The Effect of \u03b2-Hydrogen Atoms on Iron Speciation in Cross-Couplings with Simple Iron Salts and Alkyl Grignard Reagents","volume":"58","author":"Sears","year":"2019","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"8773","DOI":"10.1021\/ja801466t","article-title":"Preparation, Structure, and Reactivity of Nonstabilized Organoiron Compounds. Implications for Iron-Catalyzed Cross Coupling Reactions","volume":"130","author":"Martin","year":"2008","journal-title":"J. Am. Chem. Soc."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"11116","DOI":"10.1002\/anie.201800364","article-title":"Iron-Catalyzed Cross-Coupling in the Synthesis of Pharmaceuticals: In Pursuit of Sustainability","volume":"57","author":"Piontek","year":"2018","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_26","doi-asserted-by":"crossref","unstructured":"de Meijere, A., Br\u00e4se, S., and Oestreich, M. (2014). Metal-Catalyzed Cross-Coupling Reactions and More, Wiley.","DOI":"10.1002\/9783527655588"},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"1417","DOI":"10.1021\/cr100327p","article-title":"Advances in Transition Metal (Pd,Ni,Fe)-Catalyzed Cross-Coupling Reactions Using Alkyl-organometallics as Reaction Partners","volume":"111","author":"Jana","year":"2011","journal-title":"Chem. Rev."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"1395","DOI":"10.1002\/adsc.201400105","article-title":"Palladium- Catalysed, Directed C-H Coupling with Organometallics","volume":"356","author":"Giri","year":"2014","journal-title":"Adv. Synth. Catal."},{"key":"ref_29","unstructured":"Trost, B.M., and Fleming, I. (1991). Comprehensive Organic Synthesis, Pergamon Press."},{"key":"ref_30","unstructured":"Hudlicky, M. (1984). Reductions in Organic Chemistry, Ellis Horwood."},{"key":"ref_31","unstructured":"Seyden-Penne, J. (1997). Reductions by Alumino and Borohydrides in Organic Synthesis, Wiley."},{"key":"ref_32","doi-asserted-by":"crossref","unstructured":"Andersson, P.G., and Munslow, I.J. (2008). Modern Reduction Methods, Wiley-VCH.","DOI":"10.1002\/9783527622115"},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"3451","DOI":"10.1021\/jm200187y","article-title":"The Medicinal Chemist\u2019s Toolbox: An Analysis of Reactions Used in the Pursuit of Drug Candidates","volume":"54","author":"Roughley","year":"2011","journal-title":"J. Med. Chem."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"4443","DOI":"10.1021\/acs.jmedchem.5b01409","article-title":"Analysis of Past and Present Synthetic Methodologies in Medicinal Chemistry: Where Have All the New Reactions Gone?","volume":"59","author":"Brown","year":"2016","journal-title":"J. Med. Chem."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"17983","DOI":"10.1021\/jacs.9b09496","article-title":"Synthesis of Benzylic Alcohols by C\u2013H Oxidation","volume":"141","author":"Tanwar","year":"2019","journal-title":"J. Am. Chem. Soc."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"2268","DOI":"10.1021\/ja412578t","article-title":"Highly Chemoselective Reduction of Amides (Primary, Secondary and Tertiary) to Alcohols using by SmI2\/H2O\/Amine under Mild Conditions","volume":"136","author":"Szostak","year":"2014","journal-title":"J. Am. Chem. Soc."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"6528","DOI":"10.1021\/acs.joc.7b00372","article-title":"Mechanistic Study of SmI2\/H2O and SmI2\/Amine\/H2O-Promoted Chemoselective Reduction of Aromatic Amides (Primary, Secondary, Tertiary) to Alcohols via Aminoketyl Radicals","volume":"82","author":"Huq","year":"2017","journal-title":"J. Org. Chem."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"2589","DOI":"10.1021\/acs.accounts.8b00410","article-title":"Well-Defined Palladium(II)-NHC (NHC = N-Heterocyclic Carbene) Precatalysts for Cross-Coupling Reactions of Amides and Esters by Selective Acyl CO\u2013X (X = N, O) Cleavage","volume":"51","author":"Shi","year":"2018","journal-title":"Acc. Chem. Res."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"914","DOI":"10.1016\/j.trechm.2020.08.001","article-title":"Amide Bond Activation: The Power of Resonance","volume":"2","author":"Li","year":"2020","journal-title":"Trends Chem."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"12746","DOI":"10.1021\/acs.chemrev.1c00225","article-title":"Acyclic Twisted Amides","volume":"121","author":"Meng","year":"2021","journal-title":"Chem. Rev."},{"key":"ref_41","doi-asserted-by":"crossref","unstructured":"Gao, P., Rahman, M., Zamalloa, A., Feliciano, J., and Szostak, M. (2022). Classes of Amides that Undergo Selective N\u2013C Amide Bond Activation: The Emergence of Ground-State Destabilization. J. Org. Chem.","DOI":"10.1021\/acs.joc.2c01094"},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"5361","DOI":"10.1039\/C7GC02690K","article-title":"Cyclic Ureas (DMI, DMPU) as Efficient, Sustainable Ligands in Iron-Catalyzed C(sp2)\u2013C(sp3) Coupling of Aryl Chlorides and Tosylates","volume":"19","author":"Bisz","year":"2017","journal-title":"Green Chem."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"1290","DOI":"10.1002\/cssc.201800142","article-title":"2-Methyltetrahydrofuran: A Green Solvent for Iron-Catalyzed Cross-Coupling Reactions","volume":"11","author":"Bisz","year":"2018","journal-title":"ChemSusChem"},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"7271","DOI":"10.1002\/ejoc.201701654","article-title":"Iron-Catalyzed C(sp2)-C(sp3) Cross-Coupling of Alkyl Grignard Reagents with Polyaromatic Tosylates","volume":"48","author":"Piontek","year":"2017","journal-title":"Eur. J. Org. Chem."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"85","DOI":"10.1002\/adsc.201800849","article-title":"Iron-Catalyzed C(sp2)\u2013C(sp3) Cross-Coupling of Chlorobenzamides with Alkyl Grignard Reagents: Development of Catalyst System, Synthetic Scope and Application","volume":"361","author":"Bisz","year":"2019","journal-title":"Adv. Synth. Catal."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"1640","DOI":"10.1021\/acs.joc.8b02886","article-title":"Iron-Catalyzed C(sp2)\u2212C(sp3) Cross-Coupling of Chlorobenzenesulfonamides with Alkyl Grignard Reagents: Entry to Alkylated Aromatics","volume":"84","author":"Bisz","year":"2019","journal-title":"J. Org. Chem."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"1196","DOI":"10.1002\/cctc.201802032","article-title":"N-Methylcaprolactam as a Dipolar Aprotic Solvent for Iron-Catalyzed Cross-Coupling Reactions: Matching Efficiency with Safer Reaction Media","volume":"11","author":"Bisz","year":"2019","journal-title":"ChemCatChem"},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"1092","DOI":"10.1039\/C8CY02374C","article-title":"Iron-Catalyzed C(sp2)\u2013C(sp3) Cross-Coupling at Low Catalyst Loading","volume":"9","author":"Bisz","year":"2019","journal-title":"Catl. Sci. Technol."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"5733","DOI":"10.1002\/cctc.201901150","article-title":"Ligand Effect on Iron-Catalyzed Cross-Coupling Reactions: Evaluation of Amides as O-Coordinating Ligands","volume":"11","author":"Bisz","year":"2019","journal-title":"ChemCatChem"},{"key":"ref_50","doi-asserted-by":"crossref","unstructured":"Bisz, E., and Szostak, M. (2020). Iron-catalyzed C(sp2)-C(sp3) Cross-Coupling of Aryl Chlorobenzoates with Alkyl Grignard Reagents. Molecules, 25.","DOI":"10.3390\/molecules25010230"},{"key":"ref_51","doi-asserted-by":"crossref","unstructured":"Bisz, E. (2021). Iron-Catalyzed Cross-Coupling Reactions of Alkyl Grignards with Aryl Chlorobenzenesulfonates. Molecules, 26.","DOI":"10.3390\/molecules26195895"},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"7515","DOI":"10.1039\/D1GC02377B","article-title":"N-Butylpyrrolidone (NBP) as a Non-Toxic Substitute for NMP in Iron-Catalyzed C(sp2)-C(sp3) Cross-Coupling of Aryl Chlorides","volume":"23","author":"Bisz","year":"2021","journal-title":"Green Chem."},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"6006","DOI":"10.1021\/acs.joc.8b00617","article-title":"Reduction and Reductive Deuteration of Tertiary Amides Mediated by Sodium Dispersions with Distinct Proton Donor-Dependent Chemoselectivity","volume":"83","author":"Zhang","year":"2018","journal-title":"J. Org. Chem."},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"3010","DOI":"10.1021\/acs.orglett.8b01036","article-title":"Transition-Metal-Free, Selective Reductive Deuteration of Terminal Alkynes with Sodium Dispersions and EtOD-d1","volume":"20","author":"Han","year":"2018","journal-title":"Org. Lett."},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"3439","DOI":"10.1021\/acs.orglett.8b00891","article-title":"A Practical and Chemoselective Ammonia-Free Birch Reduction","volume":"20","author":"Lei","year":"2018","journal-title":"Org. Lett."},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"15827","DOI":"10.1021\/acs.joc.9b02028","article-title":"Reductive Cleavage of Unactivated Carbon\u2013Cyano Bonds under Ammonia-Free Birch Conditions","volume":"84","author":"Ding","year":"2019","journal-title":"J. Org. Chem."},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"2907","DOI":"10.1021\/acs.joc.0c02829","article-title":"Synthesis of \u03b1-Deuterated Primary Amines via Reductive Deuteration of Oximes Using D2O as a Deuterium Source","volume":"86","author":"Ning","year":"2021","journal-title":"J. Org. Chem."},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"609","DOI":"10.1002\/1521-3773(20020215)41:4<609::AID-ANIE609>3.0.CO;2-M","article-title":"Iron-Catalyzed Cross-Coupling Reactions of Alkyl-Grignard Reagents with Aryl Chlorides, Tosylates, and Triflates","volume":"41","author":"Leitner","year":"2002","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"13856","DOI":"10.1021\/ja027190t","article-title":"Iron-Catalyzed Cross-Coupling Reactions","volume":"124","author":"Leitner","year":"2002","journal-title":"J. Am. Chem. Soc."},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"308","DOI":"10.1002\/anie.200390103","article-title":"A Catalytic Approach to (R)-(+)-Muscopyridine with Integrated \u201cSelf-Clearance\u201d","volume":"42","author":"Leitner","year":"2003","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_61","doi-asserted-by":"crossref","first-page":"5358","DOI":"10.1002\/anie.200352413","article-title":"Catalysis-Based Total Synthesis of Latrunculin B","volume":"42","author":"Jensen","year":"2003","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_62","doi-asserted-by":"crossref","first-page":"607","DOI":"10.1002\/anie.200804434","article-title":"Domino Iron Catalysis: Direct Aryl-Alkyl Cross-Coupling","volume":"48","author":"Czaplik","year":"2009","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_63","doi-asserted-by":"crossref","first-page":"1357","DOI":"10.1002\/anie.201106110","article-title":"Chlorostyrenes in Iron-Catalyzed Biaryl Coupling Reactions","volume":"51","year":"2012","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_64","doi-asserted-by":"crossref","first-page":"10545","DOI":"10.1002\/anie.201504524","article-title":"Iron-Catalyzed Cross-Coupling of Alkenyl Acetates","volume":"54","author":"Stein","year":"2015","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_65","doi-asserted-by":"crossref","first-page":"4945","DOI":"10.1002\/anie.201210235","article-title":"Ligand-Accelerated Iron- and Cobalt-Catalyzed Cross-Coupling Reactions between N-Heteroaryl Halides and Aryl Magnesium Reagents","volume":"52","author":"Kuzmina","year":"2013","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_66","doi-asserted-by":"crossref","first-page":"1521","DOI":"10.1002\/anie.201410069","article-title":"Elementary Steps in Iron Catalysis: Exploring the Links between Iron Alkyl and Iron Olefin Complexes for their Relevance in C\u2013H Activation and C\u2013C Bond Formation","volume":"54","author":"Casitas","year":"2015","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_67","doi-asserted-by":"crossref","first-page":"10108","DOI":"10.1002\/anie.201612299","article-title":"Two Exceptional Homoleptic Iron(IV) Tetraalkyl Complexes","volume":"56","author":"Casitas","year":"2017","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_68","unstructured":"\u00c5kesson, B. (2001). N-Methyl-2-Pyrrolidone, WHO. Available online: https:\/\/echa.europa.eu\/candidate-list-table."},{"key":"ref_69","doi-asserted-by":"crossref","first-page":"1369","DOI":"10.1002\/cssc.201100780","article-title":"2-Methyltetrahydrofuran (2-MeTHF): A Biomass-Derived Solvent with Broad Application in Organic Chemistry","volume":"5","author":"Pace","year":"2012","journal-title":"ChemSusChem"},{"key":"ref_70","doi-asserted-by":"crossref","first-page":"37","DOI":"10.1007\/s00706-016-1879-3","article-title":"Recent advancements on the use of 2-methyltetrahydrofuran in organometallic chemistry","volume":"148","author":"Monticelli","year":"2017","journal-title":"Monatsh Chem."},{"key":"ref_71","doi-asserted-by":"crossref","first-page":"499","DOI":"10.1016\/0923-2508(90)90075-2","article-title":"Antibacterial activity of phenolic compounds and aromatic alcohols","volume":"141","author":"Lucchini","year":"1990","journal-title":"Res. Microbiol."},{"key":"ref_72","doi-asserted-by":"crossref","first-page":"7744","DOI":"10.1002\/anie.200700039","article-title":"The Renaissance of H\/D Exchange","volume":"46","author":"Atzrodt","year":"2007","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_73","doi-asserted-by":"crossref","first-page":"219","DOI":"10.1038\/nrd.2016.63","article-title":"Deuterated Drugs Draw Heavier Backing","volume":"15","author":"Mullard","year":"2016","journal-title":"Nat. Rev. Drug Discov."},{"key":"ref_74","doi-asserted-by":"crossref","first-page":"1182","DOI":"10.1126\/science.aap9674","article-title":"Photoredox-catalyzed deuteration and tritiation of pharmaceutical compounds","volume":"358","author":"Loh","year":"2017","journal-title":"Science"},{"key":"ref_75","doi-asserted-by":"crossref","first-page":"1758","DOI":"10.1002\/anie.201704146","article-title":"Deuterium- and Tritium-Labelled Compounds: Applications in the Life Sciences","volume":"57","author":"Atzrodt","year":"2018","journal-title":"Angew. Chemie Int. Ed."},{"key":"ref_76","doi-asserted-by":"crossref","first-page":"5276","DOI":"10.1021\/acs.jmedchem.8b01808","article-title":"Applications of Deuterium in Medicinal Chemistry","volume":"62","author":"Pirali","year":"2019","journal-title":"J. Med. Chem."},{"key":"ref_77","doi-asserted-by":"crossref","first-page":"9517","DOI":"10.1021\/jo4016612","article-title":"Iron\/Tetramethylethylenediamine-Catalyzed Ambient-Temperature Coupling of Alkyl Grignard Reagents and Aryl Chlorides","volume":"78","author":"Rushworth","year":"2013","journal-title":"J. Org. Chem."},{"key":"ref_78","doi-asserted-by":"crossref","first-page":"3178","DOI":"10.1016\/j.tetlet.2012.04.048","article-title":"Dehydrogenative amide synthesis from alcohol and amine catalyzed by hydrotalcite-supported gold nanoparticles","volume":"53","author":"Zhu","year":"2012","journal-title":"Tetrahedron Lett."},{"key":"ref_79","doi-asserted-by":"crossref","first-page":"425","DOI":"10.1071\/C96180","article-title":"Synthesis and Characterization of Stilbene Derivatives for Possible Incorporation as Smart Additives in Polymers Used as Packaging Films","volume":"50","author":"Day","year":"1997","journal-title":"Aust. J. Chem."},{"key":"ref_80","first-page":"1411","article-title":"Syntheses in the phenylcyclohexane series","volume":"6","author":"Bodroux","year":"1939","journal-title":"Bull. Soc. Chim. Fr."},{"key":"ref_81","doi-asserted-by":"crossref","first-page":"1079","DOI":"10.1016\/0040-4020(89)80018-3","article-title":"Allyl-and benzylstannanes, new reagents in terpenic synthesis","volume":"45","author":"Andrianome","year":"1989","journal-title":"Tetrahedron"}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/28\/1\/223\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T01:52:15Z","timestamp":1760147535000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/28\/1\/223"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2022,12,27]]},"references-count":81,"journal-issue":{"issue":"1","published-online":{"date-parts":[[2023,1]]}},"alternative-id":["molecules28010223"],"URL":"https:\/\/doi.org\/10.3390\/molecules28010223","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2022,12,27]]}}}