{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,18]],"date-time":"2026-08-18T04:58:02Z","timestamp":1787029082022,"version":"build-2736575974"},"reference-count":67,"publisher":"MDPI AG","issue":"22","license":[{"start":{"date-parts":[[2022,11,13]],"date-time":"2022-11-13T00:00:00Z","timestamp":1668297600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100004826","name":"Natural Science Foundation of the Beijing Municipality","doi-asserted-by":"publisher","award":["2202041"],"award-info":[{"award-number":["2202041"]}],"id":[{"id":"10.13039\/501100004826","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100004826","name":"Natural Science Foundation of the Beijing Municipality","doi-asserted-by":"publisher","award":["XK1802-6"],"award-info":[{"award-number":["XK1802-6"]}],"id":[{"id":"10.13039\/501100004826","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100004826","name":"Natural Science Foundation of the Beijing Municipality","doi-asserted-by":"publisher","award":["12060093063"],"award-info":[{"award-number":["12060093063"]}],"id":[{"id":"10.13039\/501100004826","id-type":"DOI","asserted-by":"publisher"}]},{"name":"Fundamental Research Funds for the Central Universities","award":["2202041"],"award-info":[{"award-number":["2202041"]}]},{"name":"Fundamental Research Funds for the Central Universities","award":["XK1802-6"],"award-info":[{"award-number":["XK1802-6"]}]},{"name":"Fundamental Research Funds for the Central Universities","award":["12060093063"],"award-info":[{"award-number":["12060093063"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>A highly chemoselective conversion of \u03b1,\u03b2-disubstituted nitroalkenes to ketones is developed. An acid-compatible iridium catalyst serves as the key to the conversion. At a 2500 S\/C ratio, nitroalkenes were readily converted to ketones in up to 72% isolated yields. A new mechanistic mode involving the reduction of nitroalkene to nitrosoalkene and N-alkenyl hydroxylamine is proposed. This conversion is ready to amplify to a gram-scale synthesis. The pH value plays an indispensable role in controlling the chemoselectivity.<\/jats:p>","DOI":"10.3390\/molecules27227822","type":"journal-article","created":{"date-parts":[[2022,11,14]],"date-time":"2022-11-14T04:24:10Z","timestamp":1668399850000},"page":"7822","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":6,"title":["Iridium-Catalyzed and pH-Dependent Reductions of Nitroalkenes to Ketones"],"prefix":"10.3390","volume":"27","author":[{"given":"Tingting","family":"Wang","sequence":"first","affiliation":[{"name":"Department of Organic Chemistry, College of Chemistry, Beijing University of Chemical Technology, Beijing 100029, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Changmeng","family":"Liu","sequence":"additional","affiliation":[{"name":"Department of Organic Chemistry, College of Chemistry, Beijing University of Chemical Technology, Beijing 100029, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Dong","family":"Xu","sequence":"additional","affiliation":[{"name":"Department of Organic Chemistry, College of Chemistry, Beijing University of Chemical Technology, Beijing 100029, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9039-4933","authenticated-orcid":false,"given":"Jiaxi","family":"Xu","sequence":"additional","affiliation":[{"name":"Department of Organic Chemistry, College of Chemistry, Beijing University of Chemical Technology, Beijing 100029, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7050-8780","authenticated-orcid":false,"given":"Zhanhui","family":"Yang","sequence":"additional","affiliation":[{"name":"Department of Organic Chemistry, College of Chemistry, Beijing University of Chemical Technology, Beijing 100029, China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2022,11,13]]},"reference":[{"key":"ref_1","first-page":"237","article-title":"[3+2]-Annulation reactions with nitroalkenes in the synthesis of aromatic five-membered nitrogen heterocycles","volume":"23","author":"Motornov","year":"2019","journal-title":"Targets Heterocycl."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"70","DOI":"10.1002\/ajoc.201700520","article-title":"N-Heterocyclic-Carbene-Catalyzed Reactions of Nitroalkenes: Synthesizing Important Building Blocks","volume":"7","author":"Maji","year":"2018","journal-title":"Asian J. Org. Chem."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"137","DOI":"10.1021\/cr940277f","article-title":"Tandem [4+2]\/[3+2] Cycloadditions of Nitroalkenes","volume":"96","author":"Denmark","year":"1996","journal-title":"Chem. Rev."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"95","DOI":"10.1039\/cs9912000095","article-title":"Heterosubstituted nitroalkenes in synthesis","volume":"20","author":"Barrett","year":"1991","journal-title":"Chem. Soc. Rev."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"283","DOI":"10.1080\/00304948709356200","article-title":"Syntheses and Selected Reductions of Conjugated Nitroalkenes. A Review","volume":"19","author":"Kabalka","year":"1987","journal-title":"Org. Prep. Proced. Int."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"1653","DOI":"10.1002\/rcm.4563","article-title":"\u03b413C and \u03b42H isotope ratios in amphetamine synthesized from benzaldehyde and nitroethane","volume":"24","author":"Collins","year":"2010","journal-title":"Rapid. Commun. Mass. Spectrom."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"709","DOI":"10.1038\/ja.2015.137","article-title":"Oxysporizoline, an antibacterial polycyclic quinazoline alkaloid from the marine-mudflat-derived fungus Fusarium oxysporum","volume":"69","author":"Nenkep","year":"2016","journal-title":"J. Antibiot."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"7239","DOI":"10.1016\/S0040-4039(98)01596-2","article-title":"Lewis acid-mediated cyclizations of (2\u2032-amino-N\u2032-tert-butoxycarbonyl-benzylidene)-3-alkenylamines","volume":"39","author":"Frank","year":"1998","journal-title":"Tetrahedron Lett."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"655","DOI":"10.1021\/jo990843c","article-title":"Cyclizations of Substituted Benzylidene-3-alkenylamines:\u2009Synthesis of the Tricyclic Core of the Martinellines","volume":"65","author":"Frank","year":"2000","journal-title":"J. Org. Chem."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"913","DOI":"10.1081\/SCC-200051681","article-title":"Fe-HCl: An Efficient Reagent for Deprotection of Oximes as well as Selective Oxidative Hydrolysis of Nitroalkenes and Nitroalkanes to Ketones","volume":"35","author":"Pradhan","year":"2005","journal-title":"Synth. Commun."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"8","DOI":"10.1021\/jo01147a002","article-title":"Nitro Alkene Derivatives1","volume":"15","author":"Hass","year":"1950","journal-title":"J. Org. Chem."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"1567","DOI":"10.1515\/znb-1987-1214","article-title":"Darstellung und Oxidation von 2-(2,5-Dihydroxy-phenyl)-ethylamin-Derivaten, II \/ Synthesis and Oxidation of 2-(2,5-Dihydroxyphenyl)-ethylamine Derivatives, II","volume":"42","author":"Bastian","year":"1987","journal-title":"Z. Naturforsch."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"325","DOI":"10.1246\/cl.1999.325","article-title":"A Facile Procedure for the Conversion of Nitroolefins into Carbonyl Compounds Using Al-NiCl2\u00b76H2O-THF System","volume":"28","author":"Bezbarua","year":"1999","journal-title":"Chem. Lett."},{"key":"ref_14","first-page":"28","article-title":"SnCl2\u00b72H2O-Mg-H2O: A mild reagent system for the regioselective transformation of conjugated nitroalkenes to carbonyl compounds","volume":"1","author":"Das","year":"1996","journal-title":"J. Chem. Res. (S)"},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"481","DOI":"10.3184\/030823406778256360","article-title":"Microwave-assisted transformation of \u03b1,\u03b2-and \u03b2, \u03b3-unsaturated nitroalkenes into carbonyl compounds","volume":"38","author":"Das","year":"2006","journal-title":"J. Chem. Res."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"3777","DOI":"10.1016\/S0040-4039(00)89248-5","article-title":"Chromium(II) chloride reduction of \u03b1,\u03b2-unsaturated nitroalkenes. a facile route to carbonyl compounds","volume":"26","author":"Varma","year":"1985","journal-title":"Tetrahedron Lett."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"1787","DOI":"10.1246\/bcsj.64.1787","article-title":"Titanium(III) Chloride Mediated Reduction of 1-Nitro-2-phenylethenes","volume":"64","author":"Sera","year":"1991","journal-title":"Bull. Chem. Soc. Jpn."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"697","DOI":"10.3987\/R-1986-03-0697","article-title":"Titanium Trichloride Mediated Reduction of Nitrostyrenes","volume":"24","author":"Sera","year":"1986","journal-title":"Heterocycles"},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"417","DOI":"10.1016\/S0040-4039(00)81424-0","article-title":"Reaction of nitroolefins with raney nickel and sodium hypophosphite. A mild method for converting nitroolefins into ketones (or aldehydes)","volume":"24","author":"Monti","year":"1983","journal-title":"Tetrahedron Lett."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"654","DOI":"10.1055\/s-1985-31296","article-title":"Reduction of \u03b1,\u03b2-Unsaturated Nitroalkenes with Trialkylborohydrides; A Synthesis of Ketones","volume":"6\/7","author":"Mourad","year":"1985","journal-title":"Synthesis"},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"5365","DOI":"10.1016\/S0040-4039(00)96731-5","article-title":"Reduction of \u03b1,\u03b2-unsaturated nitrocompounds with tributyltin hydride","volume":"28","author":"Aizpurua","year":"1987","journal-title":"Tetrahedron Lett."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"607","DOI":"10.1246\/cl.1983.607","article-title":"Reductive Conversion of Nitro Alkenes to Ketones and\/or Oximes in an Aqueous HClO4\u2013CH2Cl2\u2013Dioxane\u2013(Pb) System","volume":"12","author":"Torii","year":"1983","journal-title":"Chem. Lett."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"616","DOI":"10.1039\/b922691e","article-title":"The flavoprotein-catalyzed reduction of aliphatic nitro-compounds represents a biocatalytic equivalent to the Nef-reaction","volume":"12","author":"Durchschein","year":"2010","journal-title":"Green Chem."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"308","DOI":"10.1016\/j.enzmictec.2007.10.009","article-title":"Reduction of aliphatic nitro groups using an obligately anaerobic whole cell biocatalyst","volume":"42","author":"Korbekandi","year":"2008","journal-title":"Enzyme Microb. Technol."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"505","DOI":"10.1002\/jccs.200200079","article-title":"Low-Valent Ruthenium Induced Simultaneous Reduction of Nitro Group and C-C Double Bond in Nitroolefin 1-Phenyl-2-Nitropropene-1","volume":"49","author":"Li","year":"2002","journal-title":"J. Chin. Chem. Soc."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"8878","DOI":"10.1039\/C4CC03942D","article-title":"Enantioselective hydrogenation of \u03b1,\u03b2-disubstituted nitroalkenes","volume":"50","author":"Li","year":"2014","journal-title":"Chem. Commun."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"3296","DOI":"10.1039\/C7GC01289F","article-title":"Iridium-catalyzed highly efficient chemoselective reduction of aldehydes in water using formic acid as the hydrogen source","volume":"19","author":"Yang","year":"2017","journal-title":"Green Chem."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"2118","DOI":"10.1039\/C8GC00348C","article-title":"Iridium-catalyzed efficient reduction of ketones in water with formic acid as a hydride donor at low catalyst loading","volume":"20","author":"Liu","year":"2018","journal-title":"Green Chem."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"9004","DOI":"10.1039\/D1OB01690C","article-title":"Iridium-catalyzed highly stereoselective deoxygenation of tertiary cycloalkanols: Stereoelectronic insights and synthetic applications","volume":"19","author":"Wang","year":"2021","journal-title":"Org. Biomol. Chem."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"9320","DOI":"10.1021\/acscatal.8b02495","article-title":"Iridium-Catalyzed Highly Efficient and Site-Selective Deoxygenation of Alcohols","volume":"8","author":"Yang","year":"2018","journal-title":"ACS Catal."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"5496","DOI":"10.1002\/adsc.202000821","article-title":"Iridium-Catalysed Reductive Deoxygenation of Ketones with Formic Acid as Traceless Hydride Donor","volume":"362","author":"Yang","year":"2020","journal-title":"Adv. Synth. Catal."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"2088","DOI":"10.1039\/C9GC00654K","article-title":"Iridium-catalysed highly selective reduction\u2013elimination of steroidal 4-en-3-ones to 3,5-dienes in water","volume":"21","author":"Li","year":"2019","journal-title":"Green Chem."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"6050","DOI":"10.1039\/D1GC01907D","article-title":"Iridium-catalyzed highly chemoselective and efficient reduction of nitroalkenes to nitroalkanes in water","volume":"23","author":"Xu","year":"2021","journal-title":"Green Chem."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"4095","DOI":"10.1021\/acs.organomet.7b00634","article-title":"Harnessing the Reactivity of Iridium Hydrides by Air: Iridium-Catalyzed Oxidation of Aldehydes to Acids in Water","volume":"36","author":"Yang","year":"2017","journal-title":"Organometallics"},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"12001","DOI":"10.1021\/acs.joc.2c01006","article-title":"Iridium-Catalyzed Stereoselective Transfer Hydrogenation of 1,5-Benzodiazepines","volume":"87","author":"Liu","year":"2022","journal-title":"J. Org. Chem."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"3025","DOI":"10.1021\/acs.organomet.9b00353","article-title":"Highly pH-Dependent Chemoselective Transfer Hydrogenation of \u03b1,\u03b2-Unsaturated Aldehydes in Water","volume":"38","author":"Luo","year":"2019","journal-title":"Organometallics"},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"1999","DOI":"10.1039\/C8GC03744B","article-title":"Cooperative iridium complex-catalyzed synthesis of quinoxalines, benzimidazoles and quinazolines in water","volume":"21","author":"Chakrabarti","year":"2019","journal-title":"Green Chem."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"4430","DOI":"10.1021\/acs.joc.0c00157","article-title":"Synthesis of Lactams via Ir-Catalyzed C\u2013H Amidation Involving Ir-Nitrene Intermediates","volume":"85","author":"Liu","year":"2020","journal-title":"J. Org. Chem."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"1855","DOI":"10.1055\/s-0037-1611899","article-title":"Nitrosoalkenes: Underappreciated Reactive Intermediates for Formation of Carbon\u2013Carbon Bonds","volume":"30","author":"Weinreb","year":"2019","journal-title":"Synlett"},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"11324","DOI":"10.1021\/acs.chemrev.8b00375","article-title":"Recent Advances in the Chemistry of Conjugated Nitrosoalkenes and Azoalkenes","volume":"118","author":"Lopes","year":"2018","journal-title":"Chem. Rev."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"2214","DOI":"10.3762\/bjoc.13.220","article-title":"Conjugated nitrosoalkenes as Michael acceptors in carbon\u2013carbon bond forming reactions: A review and perspective","volume":"13","author":"Boyko","year":"2017","journal-title":"Beilstein J. Org. Chem."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"4098","DOI":"10.3390\/molecules14104098","article-title":"Addition and Cycloaddition Reactions of Phosphinyl- and Phosphonyl-2H-Azirines, Nitrosoalkenes and Azoalkenes","volume":"14","author":"Lemos","year":"2009","journal-title":"Molecules"},{"key":"ref_43","first-page":"371","article-title":"Product Subclass 2: 1-Nitrosoalkenes","volume":"33","author":"Reissig","year":"2007","journal-title":"Sci. Synth."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"326","DOI":"10.1126\/science.aan6245","article-title":"MOF-derived cobalt nanoparticles catalyze a general synthesis of amines","volume":"358","author":"Jagadeesh","year":"2017","journal-title":"Science"},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"2582","DOI":"10.1002\/adsc.201900179","article-title":"Stereoselective Synthesis of 1-Arylpropan-2-amines from Allylbenzenes through a Wacker-Tsuji Oxidation-Biotransamination Sequential Process","volume":"361","author":"Gotor","year":"2019","journal-title":"Adv. Synth. Catal."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"8171","DOI":"10.1039\/c1ob06251d","article-title":"Enzymatic enantiomeric resolution of phenylethylamines structurally related to amphetamine","volume":"9","author":"Rodriguez","year":"2011","journal-title":"Org. Biomo. Chem."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"2794","DOI":"10.1039\/C5GC00525F","article-title":"Broadening the chemical scope of laccases: Selective deprotection of N-benzyl groups","volume":"17","author":"Gotor","year":"2015","journal-title":"Green Chem."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"1140","DOI":"10.1021\/acscatal.8b04524","article-title":"Amine Transaminase from Exophiala Xenobiotica\u2014Crystal Structure and Engineering of a Fold IV Transaminase that Naturally Converts Biaryl Ketones","volume":"9","author":"Telzerow","year":"2019","journal-title":"ACS Catal."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"4768","DOI":"10.1021\/acscatal.7b01543","article-title":"Hybrid Organo- and Biocatalytic Process for the Asymmetric Transformation of Alcohols into Amines in Aqueous Medium","volume":"7","author":"Liardo","year":"2017","journal-title":"ACS Catal."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"55","DOI":"10.1016\/j.forsciint.2016.03.034","article-title":"The synthesis and investigation of impurities found in Clandestine Laboratories: Baeyer\u2013Villiger Route Part I.; Synthesis of P2P from benzaldehyde and methyl ethyl ketone","volume":"263","author":"Doughty","year":"2016","journal-title":"Forensic Sci. Int."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"7342","DOI":"10.1021\/ac9005588","article-title":"Characterization of Route Specific Impurities Found in Methamphetamine Synthesized by the Leuckart and Reductive Amination Methods","volume":"81","author":"Kunalan","year":"2009","journal-title":"Anal. Chem."},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"4183","DOI":"10.1016\/S0040-4039(01)86538-2","article-title":"Synthesis of secondary methylalkylamines","volume":"20","author":"Repke","year":"1979","journal-title":"Tetrahedron Lett."},{"key":"ref_53","first-page":"134","article-title":"Synthesis of 2-amino-1-phenylpropanes","volume":"9","author":"Su","year":"1988","journal-title":"Gaodeng Xuexiao Huaxue Xuebao"},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"2827","DOI":"10.1002\/cjoc.201201094","article-title":"Ethylenediamine: A Highly Effective Catalyst for One-Pot Synthesis of Aryl Nitroalkenes via Henry Reaction and Dehydration","volume":"30","author":"Yang","year":"2012","journal-title":"Chin. J. Chem."},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"31","DOI":"10.1016\/j.ejmech.2013.12.029","article-title":"Arylnitroalkenes as scavengers of macrophage-generated oxidants","volume":"74","author":"Celano","year":"2014","journal-title":"Eur. J. Med. Chem."},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"11060","DOI":"10.1021\/acs.joc.0c01322","article-title":"Asymmetric Synthesis of Merck\u2019s Potent hNK1 Antagonist and Its Stereoisomers via Tandem Acylation\/[3,3]-Rearrangement of 1,2-Oxazine N-Oxides","volume":"85","author":"Dorokhov","year":"2020","journal-title":"J. Org. Chem."},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"472","DOI":"10.1246\/cl.2007.472","article-title":"Oxidative Cleavage of Nitroalkenes with Hydrogen Peroxide in Environmentally Acceptable Solvents","volume":"36","author":"Bortolini","year":"2007","journal-title":"Chem. Lett."},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"1221","DOI":"10.1055\/s-2008-1067002","article-title":"Development of a Robust and Practical Process for the Darzens Condensation and \u03b1,\u03b2-Epoxide Rearrangement: Scope and Limitations of the Methodology","volume":"2008","author":"Zimbron","year":"2008","journal-title":"Synthesis"},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"13559","DOI":"10.1021\/acs.joc.1c01621","article-title":"Photoredox-Catalyzed Dehydrogenative Csp3\u2013Csp2 Cross-Coupling of Alkylarenes to Aldehydes in Flow","volume":"86","author":"Griffiths","year":"2021","journal-title":"J. Org. Chem."},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"53","DOI":"10.1016\/S0379-0738(00)00311-X","article-title":"Synthesis of 4-methyl-5-arylpyrimidines and 4-arylpyrimidines: Route specific markers for the Leuckardt preparation of amphetamine, 4-methoxyamphetamine, and 4-methylthioamphetamine","volume":"115","author":"Kirkbride","year":"2001","journal-title":"Forensic Sci. Int."},{"key":"ref_61","doi-asserted-by":"crossref","first-page":"8273","DOI":"10.1021\/ja1033777","article-title":"Copper Catalyzed Arylation\/C\u2212C Bond Activation: An Approach toward \u03b1-Aryl Ketones","volume":"132","author":"He","year":"2010","journal-title":"J. Am. Chem. Soc."},{"key":"ref_62","doi-asserted-by":"crossref","first-page":"5246","DOI":"10.1021\/acs.orglett.0c01915","article-title":"Direct Synthesis of Propen-2-yl Sulfones through Cascade Reactions Using Calcium Carbide as an Alkyne Source","volume":"22","author":"Gao","year":"2020","journal-title":"Org. Lett."},{"key":"ref_63","doi-asserted-by":"crossref","first-page":"427","DOI":"10.1021\/acs.orglett.0c03935","article-title":"Photoinduced Cross-Coupling of Aryl Iodides with Alkenes","volume":"23","author":"Liu","year":"2021","journal-title":"Org. Lett."},{"key":"ref_64","doi-asserted-by":"crossref","first-page":"2773","DOI":"10.1002\/adsc.201800427","article-title":"Salicylic Acid-Catalyzed Arylation of Enol Acetates with Anilines","volume":"360","year":"2018","journal-title":"Adv. Synth. Catal."},{"key":"ref_65","doi-asserted-by":"crossref","first-page":"5445","DOI":"10.1016\/j.bmcl.2012.07.042","article-title":"Development of isoform selective PI3-kinase inhibitors as pharmacological tools for elucidating the PI3K pathway","volume":"22","author":"Bruce","year":"2012","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_66","unstructured":"Capraro, H.-G., Furet, P., Imbach, P., and Stauffer, F. (2007). Imidazopyridazines as PI3K lipid kinase inhibitors. (WO2007EP09381)."},{"key":"ref_67","doi-asserted-by":"crossref","first-page":"242","DOI":"10.1246\/bcsj.57.242","article-title":"Arylation and 1-Alkenylation on \u03b1-Position of Ketones via Tributyltin Enolates Catalyzed by Palladium Complex","volume":"57","author":"Kosugi","year":"1984","journal-title":"Bull. Chem. Soc. Jpn."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/27\/22\/7822\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T01:17:24Z","timestamp":1760145444000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/27\/22\/7822"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2022,11,13]]},"references-count":67,"journal-issue":{"issue":"22","published-online":{"date-parts":[[2022,11]]}},"alternative-id":["molecules27227822"],"URL":"https:\/\/doi.org\/10.3390\/molecules27227822","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2022,11,13]]}}}