{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,9]],"date-time":"2026-09-09T01:05:04Z","timestamp":1788915904889,"version":"build-2803163510"},"reference-count":77,"publisher":"MDPI AG","issue":"19","license":[{"start":{"date-parts":[[2021,9,30]],"date-time":"2021-09-30T00:00:00Z","timestamp":1632960000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/100000001","name":"National Science Foundation","doi-asserted-by":"publisher","award":["NSF CHE-1900340"],"award-info":[{"award-number":["NSF CHE-1900340"]}],"id":[{"id":"10.13039\/100000001","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Herein, we report a Kumada cross-coupling reaction of benzylic sulfonamides. The scope of the transformation includes acyclic and cyclic sulfonamide precursors that cleanly produce highly substituted acyclic fragments. Preliminary data are consistent with a stereospecific mechanism that allows for a diastereoselective reaction.<\/jats:p>","DOI":"10.3390\/molecules26195947","type":"journal-article","created":{"date-parts":[[2021,10,8]],"date-time":"2021-10-08T21:23:55Z","timestamp":1633728235000},"page":"5947","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":3,"title":["Nickel-Catalyzed Kumada Cross-Coupling Reactions of Benzylic Sulfonamides"],"prefix":"10.3390","volume":"26","author":[{"given":"Kirsten A.","family":"Hewitt","sequence":"first","affiliation":[{"name":"Department of Chemistry, University of California, Irvine, CA 92697-2025, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Claire A.","family":"Herbert","sequence":"additional","affiliation":[{"name":"Department of Chemistry, University of California, Irvine, CA 92697-2025, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4243-7089","authenticated-orcid":false,"given":"Alissa C.","family":"Matus","sequence":"additional","affiliation":[{"name":"Department of Chemistry, University of California, Irvine, CA 92697-2025, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2818-4038","authenticated-orcid":false,"given":"Elizabeth R.","family":"Jarvo","sequence":"additional","affiliation":[{"name":"Department of Chemistry, University of California, Irvine, CA 92697-2025, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2021,9,30]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","unstructured":"De Meijere, A., and Diederich, F. (2004). Metal-Catalyzed Cross-Coupling Reactions, Wiley-VCH. [2nd ed.].","DOI":"10.1002\/9783527619535"},{"key":"ref_2","unstructured":"Hartwig, J.F. (2010). Organotransition Metal Chemistry: From Bonding to Catalysis, University Science Books."},{"key":"ref_3","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_4","doi-asserted-by":"crossref","first-page":"9587","DOI":"10.1021\/acs.chemrev.5b00162","article-title":"Enantioselective and Enantiospecific Transition-Metal-Catalyzed Cross-Coupling Reactions of Organometallic Reagents to Construct C\u2013C bonds","volume":"115","author":"Cherney","year":"2015","journal-title":"Chem. Rev."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"eaaf7230","DOI":"10.1126\/science.aaf7230","article-title":"Transition Metal-Catalyzed Alkyl-Alkyl Bond Formation: Another Dimension in Cross-Coupling Chemistry","volume":"356","author":"Choi","year":"2017","journal-title":"Science"},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1021\/acs.organomet.8b00720","article-title":"Cross-Coupling and Related Reactions: Connecting Past Successes to the Development of New Reactions for the Future","volume":"38","author":"Campeau","year":"2019","journal-title":"Organometallics"},{"key":"ref_7","doi-asserted-by":"crossref","unstructured":"Tamaru, Y. (2005). Modern Organonickel Chemistry, Wiley-VCH.","DOI":"10.1002\/3527604847"},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"299","DOI":"10.1038\/nature13274","article-title":"Recent Advances in Homogeneous Nickel Catalysis","volume":"509","author":"Tasker","year":"2014","journal-title":"Nature"},{"key":"ref_9","doi-asserted-by":"crossref","unstructured":"Ogoshi, S. (2020). Nickel Catalysis in Organic Synthesis: Methods and Reactions, Wiley.","DOI":"10.1002\/9783527813827"},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"1802","DOI":"10.1021\/acs.oprd.1c00241","article-title":"Recent Advances in Nonprecious Metal Catalysis","volume":"25","author":"Singer","year":"2021","journal-title":"Org. Process. Res. Dev."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"1346","DOI":"10.1021\/cr100259t","article-title":"Nickel-Catalyzed Cross-Couplings Involving Carbon-Oxygen Bonds","volume":"111","author":"Rosen","year":"2011","journal-title":"Chem. Rev."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"2344","DOI":"10.1021\/acs.accounts.5b00223","article-title":"Stereospecific Nickel-Catalyzed Cross-Coupling Reactions of Benzylic Ethers and Esters","volume":"48","author":"Tollefson","year":"2015","journal-title":"Acc. Chem. Res."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"1486","DOI":"10.1021\/ar100082d","article-title":"Exploration of New C\u2013O Electrophiles in Cross-Coupling Reactions","volume":"43","author":"Yu","year":"2010","journal-title":"Acc. Chem. Res."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"12045","DOI":"10.1021\/acs.chemrev.5b00386","article-title":"Transition-Metal-Catalyzed Cleavage of C\u2013N Single Bonds","volume":"115","author":"Ouyang","year":"2015","journal-title":"Chem. Rev."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"1257","DOI":"10.1039\/C5CS00534E","article-title":"Transition-Metal Catalysed C\u2013N Bond Activation","volume":"45","author":"Wang","year":"2016","journal-title":"Chem. Soc. Rev."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"12286","DOI":"10.1039\/C8CC07093H","article-title":"Asymmetric Synthesis via Stereospecific C\u2013N and C\u2013O Bond Activation of Alkyl Amine and Alcohol Derivatives","volume":"54","author":"Pound","year":"2018","journal-title":"Chem. Commun."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"1413","DOI":"10.1021\/acscatal.6b03277","article-title":"Breaking Amides using Nickel Catalysis","volume":"7","author":"Dander","year":"2017","journal-title":"ACS Catal."},{"key":"ref_18","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_19","doi-asserted-by":"crossref","first-page":"1980","DOI":"10.1002\/adsc.201100285","article-title":"Cross-Coupling of Grignard Reagents with Sulfonyl-Activated sp3 Carbon-Nitrogen Bonds","volume":"353","author":"Li","year":"2011","journal-title":"Adv. Synth. Catal."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"8153","DOI":"10.1021\/cr500036t","article-title":"The Chemistry of Transition Metals with Three-Membered Ring Heterocycles","volume":"114","author":"Huang","year":"2014","journal-title":"Chem. Rev."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"2890","DOI":"10.1021\/ja017652n","article-title":"Interactions of Aziridines with Nickel Complexes:\u2009 Oxidative-Addition and Reductive-Elimination Reactions that Break and Make C\u2212N Bonds","volume":"124","author":"Lin","year":"2002","journal-title":"J. Am. Chem. Soc."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"9541","DOI":"10.1021\/ja3013825","article-title":"Nickel-Catalyzed Negishi Alkylations of Styrenyl Aziridines","volume":"134","author":"Huang","year":"2012","journal-title":"J. Am. Chem. Soc."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"5638","DOI":"10.1021\/jacs.5b02503","article-title":"Electron-Deficient Olefin Ligands Enable Generation of Quaternary Carbons by Ni-Catalyzed Cross Coupling","volume":"137","author":"Huang","year":"2015","journal-title":"J. Am. Chem. Soc."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"13605","DOI":"10.1021\/ja4076716","article-title":"Directed Nickel-Catalyzed Negishi Cross Coupling of Alkyl Aziridines","volume":"135","author":"Nielsen","year":"2013","journal-title":"J. Am. Chem. Soc."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"11145","DOI":"10.1021\/ja505823s","article-title":"Highly Regioselective Nickel-Catalyzed Cross-Coupling of N-Tosylaziridines and Alkylzinc Reagents","volume":"136","author":"Jensen","year":"2014","journal-title":"J. Am. Chem. Soc."},{"key":"ref_26","doi-asserted-by":"crossref","unstructured":"Wenkert, E., Han, A.-L., and Jenny, C.-J. (1988). Nickel-Induced Conversion of Carbon-Nitrogen into Carbon-Carbon Bonds. One-Step Transformations of Aryl, Quaternary Ammonium Salts into Alkylarenes and Biaryls. J. Chem. Soc. Chem. Commun., 975\u2013976.","DOI":"10.1039\/C39880000975"},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"6046","DOI":"10.1021\/ja034908b","article-title":"The First Suzuki Cross-Couplings of Aryltrimethylammonium Salts","volume":"125","author":"Blakey","year":"2003","journal-title":"J. Am. Chem. Soc."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"280","DOI":"10.1021\/ja3089422","article-title":"Nickel-Catalyzed Cross-Couplings of Benzylic Ammonium Salts and Boronic Acids: Stereospecific Formation of Diarylethanes via C\u2013N Bond Activation","volume":"135","author":"Maity","year":"2013","journal-title":"J. Am. Chem. Soc."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"4257","DOI":"10.1016\/j.tet.2014.03.039","article-title":"A General, Simple Catalyst for Enantiospecific Cross Couplings of Benzylic Ammonium Triflates and Boronic Acids: No Phosphine Ligand Required","volume":"70","author":"Roberts","year":"2014","journal-title":"Tetrahedron"},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"4450","DOI":"10.1016\/j.tet.2017.06.004","article-title":"Nickel-Catalyzed Cross-Coupling of Aryl or -2-Menaphthyl Quaternary Ammonium Triflates with Organoaluminum Reagents","volume":"73","author":"He","year":"2017","journal-title":"Tetrahedron"},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"2691","DOI":"10.1016\/S0040-4039(00)77797-5","article-title":"Pyridines as Leaving Groups in Synthetic Transformations: Nucleophilic Displacements of Amino Groups, and Novel Preparations of Nitriles and Isocyanate","volume":"17","author":"Bapat","year":"1976","journal-title":"Tetrahedron Lett."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"25","DOI":"10.1016\/0040-4020(81)85037-5","article-title":"Carbon-Alkylation of Simple Nitronate Anions by N-Substituted Pyridiniums","volume":"37","author":"Katritzky","year":"1981","journal-title":"Tetrahedron"},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"420","DOI":"10.1002\/anie.198404201","article-title":"Pyrylium Mediated Transformations of Primary Amino Groups into Other Functional Groups. New Synthetic Methods (41)","volume":"23","author":"Katritzky","year":"1984","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"1947","DOI":"10.1016\/S0957-4166(01)00343-3","article-title":"Stereoselective Transformation of Amines via Chiral 2,4,6-Triphenylpyridinium Intermediates","volume":"12","author":"Said","year":"2001","journal-title":"Tetrahedron Asymmetry"},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"12336","DOI":"10.1002\/anie.201706896","article-title":"Deaminative Strategy for the Visible-Light-Mediated Generation of Alkyl Radicals","volume":"56","author":"Klauck","year":"2017","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"8943","DOI":"10.1021\/acscatal.9b03084","article-title":"Recent Advances in Pyridinium Salts as Radical Reservoirs in Organic Synthesis","volume":"9","author":"He","year":"2019","journal-title":"ACS Catal."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"489","DOI":"10.1055\/s-0039-1690703","article-title":"Pyrylium Salts: Selective Reagents for the Activation of Primary Amino Groups in Organic Synthesis","volume":"52","author":"Pang","year":"2020","journal-title":"Synthesis"},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"9264","DOI":"10.1002\/anie.201911660","article-title":"Pyridinium Salts as Redox-Active Functional Group Transfer Reagents","volume":"59","author":"Jelier","year":"2020","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"1215","DOI":"10.1002\/ejoc.202001193","article-title":"Recent Developments in Deaminative Functionalization of Alkyl Amines","volume":"2021","author":"Li","year":"2021","journal-title":"Eur. J. Org. Chem."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"473","DOI":"10.1038\/s41929-019-0292-9","article-title":"Radical Coupling from Alkyl Amines","volume":"2","author":"Kong","year":"2019","journal-title":"Nat. Catal."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"5313","DOI":"10.1021\/jacs.7b02389","article-title":"Harnessing Alkyl Amines as Electrophiles for Nickel-Catalyzed Cross Couplings via C\u2013N Bond Activation","volume":"139","author":"Basch","year":"2017","journal-title":"J. Am. Chem. Soc."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"7356","DOI":"10.1021\/acs.orglett.9b02643","article-title":"Deaminative Arylation of Amino Acid-Derived Pyridinium Salts","volume":"21","author":"Hoerner","year":"2019","journal-title":"Org. Lett."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"3030","DOI":"10.1021\/acs.orglett.8b01062","article-title":"Transforming Benzylic Amines into Diarylmethanes: Cross-Couplings of Benzylic Pyridinium Salts via C\u2013N Bond Activation","volume":"20","author":"Liao","year":"2018","journal-title":"Org. Lett."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"9738","DOI":"10.1021\/acs.orglett.9b03899","article-title":"Engaging Alkenes and Alkynes in Deaminative Alkyl\u2013Alkyl and Alkyl\u2013Vinyl Cross-Couplings of Alkylpyridinium Salts","volume":"21","author":"Baker","year":"2019","journal-title":"Org. Lett."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"3231","DOI":"10.1055\/s-0037-1610084","article-title":"Vinylation of Benzylic Amines via C\u2013N Bond Functionalization of Benzylic Pyridinium Salts","volume":"50","author":"Guan","year":"2018","journal-title":"Synthesis"},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"2257","DOI":"10.1021\/jacs.9b00111","article-title":"Harnessing Alkylpyridinium Salts as Electrophiles in Deaminative Alkyl\u2013Alkyl Cross-Couplings","volume":"141","author":"Plunkett","year":"2019","journal-title":"J. Am. Chem. Soc."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"389","DOI":"10.1021\/ja108547u","article-title":"Stereospecific Nickel-Catalyzed Cross-Coupling Reactions of Alkyl Ethers: Enantioselective Synthesis of Diarylethanes","volume":"133","author":"Taylor","year":"2011","journal-title":"J. Am. Chem. Soc."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"14951","DOI":"10.1021\/ja5076426","article-title":"Stereospecific Cross-Coupling Reactions of Aryl-Substituted Tetrahydrofurans, Tetrahydropyrans, and Lactones","volume":"136","author":"Tollefson","year":"2014","journal-title":"J. Am. Chem. Soc."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"940","DOI":"10.1039\/c39750000940","article-title":"Leaving Group Ability in Base-Promoted Alkene-Forming 1,2-Eliminations","volume":"23","author":"Marshall","year":"1975","journal-title":"J. Chem. Soc. Chem. Commun."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"1775","DOI":"10.1021\/acs.joc.9b02603","article-title":"Engaging Sulfonamides: Intramolecular Cross-Electrophile Coupling Reaction of Sulfonamides with Alkyl Chlorides","volume":"85","author":"Lucas","year":"2020","journal-title":"J. Org. Chem."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"7598","DOI":"10.1021\/jacs.0c01724","article-title":"Synthesis of \u03b2-Phenethylmines via Ni\/Photoredox Cross-Electrophile Coupling of Aliphatic Aziridines and Aryl Iodides","volume":"142","author":"Steinman","year":"2020","journal-title":"J. Am. Chem. Soc."},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"8456","DOI":"10.1021\/acscatal.1c01860","article-title":"Dissection of Alkylpyridinium Structures to Understand Deamination Reactions","volume":"11","author":"Tcyrulnikov","year":"2021","journal-title":"ACS Catal."},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"1604","DOI":"10.1021\/acscatal.0c05484","article-title":"Nickel-Catalyzed, Stereospecific C\u2212C and C\u2212B Cross-Couplings via C\u2212N and C\u2212O Bond Activation","volume":"11","author":"Xu","year":"2021","journal-title":"ACS Catal."},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"5053","DOI":"10.1002\/anie.201600697","article-title":"Nickel-Catalyzed Carboxylation of Benzylic C\u2013N Bonds with CO2","volume":"55","author":"Moragas","year":"2016","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"1057","DOI":"10.1055\/s-2006-926376","article-title":"The Iterative Synthesis of Acyclic Deoxypropionate Units and Their Implication in Polyketide-Derived Natural Products","volume":"7","author":"Hanessian","year":"2006","journal-title":"Synthesis"},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"14198","DOI":"10.1002\/anie.202003735","article-title":"Conformational Design Principles in Total Synthesis","volume":"59","author":"Chen","year":"2020","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"2012","DOI":"10.1021\/om500156q","article-title":"A Broadly Applicable Strategy for Entry into Homogenous Nickel(0) Catalysts from Air-Stable Nickel(II) Complexes","volume":"33","author":"Standley","year":"2014","journal-title":"Organometallics"},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"3044","DOI":"10.1002\/chem.202000215","article-title":"Identification of the Active Catalyst for Nickel-Catalyzed Stereospecific Kumada Coupling Reactions of Ethers","volume":"26","author":"Dawson","year":"2020","journal-title":"Chem. Eur. J."},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"7474","DOI":"10.1021\/acs.orglett.8b03249","article-title":"FeCl3 as an Ion-Pairing Lewis Acid Catalyst. Formation of Highly Lewis Acidic FeCl2+ and Thermodynamically Stable FeCl4\u2013 To Catalyze the Aza-Diels\u2013Alder Reaction with High Turnover Frequency","volume":"20","author":"Tomifuji","year":"2018","journal-title":"Org. Lett."},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"967","DOI":"10.1002\/hlca.200800355","article-title":"Stereoselective Routes for the Total Synthesis of (+)-Crytocarya Diacetate","volume":"92","author":"Sabitha","year":"2009","journal-title":"Helv. Chim. Acta"},{"key":"ref_61","doi-asserted-by":"crossref","first-page":"9760","DOI":"10.1021\/jacs.5b03870","article-title":"Stereospecific Intramolecular Reductive Cross-Electrophile Coupling Reactions for Cyclopropane Synthesis","volume":"137","author":"Tollefson","year":"2015","journal-title":"J. Am. Chem. Soc."},{"key":"ref_62","doi-asserted-by":"crossref","first-page":"1541","DOI":"10.1246\/cl.1981.1541","article-title":"The Reaction of Benzylated Pyrrole and Adenine Ribonucleosides with Grignard Reagents","volume":"10","author":"Kawana","year":"1981","journal-title":"Chem. Lett."},{"key":"ref_63","doi-asserted-by":"crossref","first-page":"1576","DOI":"10.1002\/anie.201711429","article-title":"A Non-Competitive Inhibitor of VCP\/p97 and VPS4 Reveals Conserved Allosteric Circuits in Type I and II AAA ATPases","volume":"57","author":"Krahn","year":"2018","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_64","doi-asserted-by":"crossref","first-page":"751","DOI":"10.1126\/science.282.5389.751","article-title":"An MTP Inhibitor That Normalizes Atherogenic Lipoprotein Levels in WHHL Rabbits","volume":"282","author":"Wetterau","year":"1998","journal-title":"Science"},{"key":"ref_65","doi-asserted-by":"crossref","first-page":"1621","DOI":"10.1016\/S0968-0896(03)00061-0","article-title":"Syntheses of Novel Diphenyl Piperazine Derivatives and Their Activities as Inhibitors of Dopamine Uptake in the Central Nervous System","volume":"11","author":"Kimura","year":"2003","journal-title":"Bioorg. Med. Chem."},{"key":"ref_66","doi-asserted-by":"crossref","first-page":"7","DOI":"10.1016\/j.ejmech.2018.01.092","article-title":"Design and synthesis of new potent N,N-is(arylalkyl)piperazine Derivatives as Multidrug Resistance (MDR) Reversing agents","volume":"147","author":"Dei","year":"2018","journal-title":"Eur. J. Med. Chem."},{"key":"ref_67","doi-asserted-by":"crossref","first-page":"893","DOI":"10.1039\/c3md00088e","article-title":"Chiral 1,1-Diaryl Compounds as Important Pharmacophores","volume":"4","author":"Ameen","year":"2013","journal-title":"MedChemComm"},{"key":"ref_68","doi-asserted-by":"crossref","first-page":"2422","DOI":"10.1002\/anie.201308666","article-title":"Stereospecific Nickel-Catalyzed Cross-Coupling Reactions of Alkyl Grignard Reagents and Identification of Selective Anti-Breast-Cancer Agents","volume":"53","author":"Yonova","year":"2014","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_69","unstructured":"When (R-BINAP)NiCl2 was employed as the precatalyst, the desired product was not observed and 44% of starting material was recovered."},{"key":"ref_70","doi-asserted-by":"crossref","first-page":"5835","DOI":"10.1021\/jacs.9b00097","article-title":"A Unified Explanation for Chemoselectivity and Stereospecificity of Ni-Catalyzed Kumada and Cross-Electrophile Coupling Reactions of Benzylic Ethers: A Combined Computational and Experimental Study","volume":"141","author":"Chen","year":"2019","journal-title":"J. Am. Chem. Soc."},{"key":"ref_71","doi-asserted-by":"crossref","first-page":"1518","DOI":"10.1021\/om9503712","article-title":"Safe and Convenient Procedure for Solvent Purification","volume":"15","author":"Pangborn","year":"1996","journal-title":"Organometallics"},{"key":"ref_72","first-page":"890","article-title":"Convenient Titration Method for Organometallic Zinc, Magnesium, and Lanthanide Reagents","volume":"5","author":"Krasoviskiy","year":"2006","journal-title":"Synthesis"},{"key":"ref_73","doi-asserted-by":"crossref","first-page":"179","DOI":"10.1021\/ol048005e","article-title":"A General Method for the Preparation of N-Sulfonyl Aldimines and Ketimines","volume":"7","author":"Parra","year":"2005","journal-title":"Org. Lett."},{"key":"ref_74","doi-asserted-by":"crossref","first-page":"348","DOI":"10.1021\/acs.orglett.5b03080","article-title":"Copper-Catalyzed Intermolecular Chloro- and Bromotrifluoromethylation of Alkenes","volume":"18","author":"Fu","year":"2016","journal-title":"Org. Lett."},{"key":"ref_75","doi-asserted-by":"crossref","first-page":"2888","DOI":"10.1021\/jo102143r","article-title":"Organocatalytic Tandem Three-Component Reaction of Imine, Alkyl Vinyl Ketone, and Imide via aza-Baylis\u2212Hillman Reaction","volume":"76","author":"Syu","year":"2011","journal-title":"J. Org. Chem."},{"key":"ref_76","doi-asserted-by":"crossref","first-page":"1392","DOI":"10.1021\/acscatal.7b04030","article-title":"A General Nickel-Catalyzed Kumada Vinylation for the Preparation of 2-Substituted 1,3-Dienes","volume":"8","author":"Fiorito","year":"2018","journal-title":"ACS Catal."},{"key":"ref_77","doi-asserted-by":"crossref","first-page":"8191","DOI":"10.1021\/acs.joc.7b00804","article-title":"Palladium-Catalyzed Intermolecular Oxidative Cyclization of Allyltosylamides with AcOH: Assembly of 3-Pyrrolin-2-ones","volume":"82","author":"Huang","year":"2017","journal-title":"J. Org. Chem."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/26\/19\/5947\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T07:07:55Z","timestamp":1760166475000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/26\/19\/5947"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2021,9,30]]},"references-count":77,"journal-issue":{"issue":"19","published-online":{"date-parts":[[2021,10]]}},"alternative-id":["molecules26195947"],"URL":"https:\/\/doi.org\/10.3390\/molecules26195947","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2021,9,30]]}}}