{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,1]],"date-time":"2026-09-01T23:16:04Z","timestamp":1788304564175,"version":"build-2803163510"},"reference-count":62,"publisher":"American Chemical Society (ACS)","issue":"49","license":[{"start":{"date-parts":[[2020,11,25]],"date-time":"2020-11-25T00:00:00Z","timestamp":1606262400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/pubs.acs.org\/page\/policy\/authorchoice_ccby_termsofuse.html"}],"funder":[{"DOI":"10.13039\/100010663","name":"H2020 European Research Council","doi-asserted-by":"publisher","award":["AdG 692775"],"award-info":[{"award-number":["AdG 692775"]}],"id":[{"id":"10.13039\/100010663","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2020,12,9]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>Selective oxidative deamination has long been considered to be an important but challenging transformation, although it is a common critical process in the metabolism of bioactive amino compounds. Most of the synthetic methods developed so far rely on the use of stoichiometric amounts of strong and toxic oxidants. Here we present a green and efficient method for oxidative deamination, using water as the oxidant, catalyzed by a ruthenium pincer complex. This unprecedented reaction protocol liberates hydrogen gas and avoids the use of sacrificial oxidants. A wide variety of primary amines are selectively transformed to carboxylates or ketones in good to high yields. It is noteworthy that mechanistic experiments and DFT calculations indicate that in addition to serving as the oxidant, water also plays an important role in assisting the hydrogen liberation steps involved in amine dehydrogenation.<\/jats:p>","DOI":"10.1021\/jacs.0c10826","type":"journal-article","created":{"date-parts":[[2020,11,25]],"date-time":"2020-11-25T15:22:53Z","timestamp":1606317773000},"page":"20875-20882","source":"Crossref","is-referenced-by-count":45,"title":["Catalytic\nOxidative Deamination by Water with H2 Liberation"],"prefix":"10.1021","volume":"142","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-5662-8401","authenticated-orcid":true,"given":"Shan","family":"Tang","sequence":"first","affiliation":[{"name":"Weizmann Institute of Science , , ,","place":["Rehovot, Israel, 76100"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Michael","family":"Rauch","sequence":"additional","affiliation":[{"name":"Weizmann Institute of Science , , ,","place":["Rehovot, Israel, 76100"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6700-1727","authenticated-orcid":true,"given":"Michael","family":"Montag","sequence":"additional","affiliation":[{"name":"Weizmann Institute of Science , , ,","place":["Rehovot, Israel, 76100"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9008-8477","authenticated-orcid":true,"given":"Yael","family":"Diskin-Posner","sequence":"additional","affiliation":[{"name":"Weizmann Institute of Science , , ,","place":["Rehovot, Israel, 76100"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yehoshoa","family":"Ben-David","sequence":"additional","affiliation":[{"name":"Weizmann Institute of Science , , ,","place":["Rehovot, Israel, 76100"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2320-0262","authenticated-orcid":true,"given":"David","family":"Milstein","sequence":"additional","affiliation":[{"name":"Weizmann Institute of Science , , ,","place":["Rehovot, Israel, 76100"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2020,11,25]]},"reference":[{"key":"2026090118405552000_cit1","volume-title":"Amines: Synthesis\nProperties and Applications","author":"Lawrence","year":"2004"},{"key":"2026090118405552000_cit2","doi-asserted-by":"publisher","first-page":"635","DOI":"10.1126\/science.1191843","article-title":"The Give and\nTake of Alcohol Activation","volume":"329","author":"Watson","year":"2010","journal-title":"Science"},{"key":"2026090118405552000_cit3","doi-asserted-by":"publisher","first-page":"5472","DOI":"10.1002\/anie.200352503","article-title":"Highly\nEnantioselective Hydrogen-Transfer Reductive\nAmination: Catalytic Asymmetric Synthesis of Primary Amines","volume":"42","author":"Kadyrov","year":"2003","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026090118405552000_cit4","doi-asserted-by":"publisher","first-page":"8661","DOI":"10.1002\/anie.200803229","article-title":"Selective Synthesis of Primary Amines Directly from\nAlcohols and Ammonia","volume":"47","author":"Gunanathan","year":"2008","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026090118405552000_cit5","doi-asserted-by":"publisher","first-page":"8126","DOI":"10.1002\/anie.201002576","article-title":"An Efficient\nand General Synthesis of Primary Amines by Ruthenium-Catalyzed Amination\nof Secondary Alcohols with Ammonia","volume":"49","author":"Imm","year":"2010","journal-title":"Angew. Chem.,\nInt. Ed."},{"key":"2026090118405552000_cit6","doi-asserted-by":"publisher","first-page":"305","DOI":"10.1126\/science.1188934","article-title":"Biocatalytic\nAsymmetric Synthesis of Chiral Amines from Ketones Applied to Sitagliptin\nManufacture","volume":"329","author":"Savile","year":"2010","journal-title":"Science"},{"key":"2026090118405552000_cit7","doi-asserted-by":"publisher","first-page":"150","DOI":"10.1002\/anie.201106737","article-title":"Platinum-Catalyzed\nDirect Amination of Allylic Alcohols\nwith Aqueous Ammonia: Selective Synthesis of Primary Allylamines","volume":"51","author":"Das","year":"2012","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026090118405552000_cit8","doi-asserted-by":"publisher","first-page":"1525","DOI":"10.1126\/science.aac9283","article-title":"Conversion\nof alcohols to enantiopure amines through dual-enzyme hydrogen-borrowing\ncascades","volume":"349","author":"Mutti","year":"2015","journal-title":"Science"},{"key":"2026090118405552000_cit9","doi-asserted-by":"publisher","first-page":"2024","DOI":"10.1021\/jacs.7b12898","article-title":"Asymmetric\nSynthesis of Chiral Primary Amines by Ruthenium-Catalyzed Direct Reductive\nAmination of Alkyl Aryl Ketones with Ammonium Salts and Molecular\nH2","volume":"140","author":"Tan","year":"2018","journal-title":"J. Am. Chem. Soc."},{"key":"2026090118405552000_cit10","doi-asserted-by":"publisher","first-page":"355","DOI":"10.1021\/jacs.7b10496","article-title":"Direct Asymmetric\nRuthenium-Catalyzed\nReductive Amination of Alkyl\u2013Aryl Ketones with Ammonia and\nHydrogen","volume":"140","author":"Gallardo-Donaire","year":"2018","journal-title":"J. Am. Chem. Soc."},{"key":"2026090118405552000_cit11","doi-asserted-by":"publisher","first-page":"14193","DOI":"10.1002\/anie.201809719","article-title":"Dynamic Kinetic\nAsymmetric Reductive Amination: Synthesis of Chiral\nPrimary \u03b2-Amino Lactams","volume":"57","author":"Lou","year":"2018","journal-title":"Angew. Chem.,\nInt. Ed."},{"key":"2026090118405552000_cit12","doi-asserted-by":"publisher","first-page":"4123","DOI":"10.1038\/s41467-018-06416-6","article-title":"Simple\nruthenium-catalyzed reductive amination enables the synthesis of a\nbroad range of primary amines","volume":"9","author":"Senthamarai","year":"2018","journal-title":"Nat. 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Commun."},{"key":"2026090118405552000_cit32","doi-asserted-by":"publisher","first-page":"613","DOI":"10.1002\/hlca.201100404","article-title":"Nicotinium Dichromate (=3-Carboxypyridinium\nDichromate; NDC) as an Efficient Reagent for the Oxidative Deamination\nof Amines and Aminophosphonates","volume":"95","author":"Sobhani","year":"2012","journal-title":"Helv. Chim.\nActa"},{"key":"2026090118405552000_cit33","doi-asserted-by":"publisher","first-page":"1429","DOI":"10.1021\/ja01034a027","article-title":"Oxidation of primary amines to ketones","volume":"91","author":"Corey","year":"1969","journal-title":"J. Am. Chem. 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Chem."},{"key":"2026090118405552000_cit36","doi-asserted-by":"publisher","first-page":"843","DOI":"10.1021\/ol802715c","article-title":"Copper\/Ascorbic Acid Dyad as a Catalytic System for\nSelective Aerobic Oxidation of Amines","volume":"11","author":"Srogl","year":"2009","journal-title":"Org.\nLett."},{"key":"2026090118405552000_cit37","doi-asserted-by":"publisher","first-page":"231","DOI":"10.1016\/S0020-1693(00)81226-8","article-title":"Pyridoxal- and metal ion-catalyzed\noxidative deamination of alpha amino acids","volume":"138","author":"Tatsumoto","year":"1987","journal-title":"Inorg. Chim. Acta"},{"key":"2026090118405552000_cit38","doi-asserted-by":"publisher","first-page":"6479","DOI":"10.1021\/ja00017a019","article-title":"Oxidative deamination of amino acids\nby molecular oxygen\nwith pyridoxal derivatives and metal ions as catalysts","volume":"113","author":"Shanbhag","year":"1991","journal-title":"J. Am. Chem. 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Res."},{"key":"2026090118405552000_cit42","doi-asserted-by":"publisher","first-page":"2624","DOI":"10.1002\/chem.201102779","article-title":"Visible-Light-Induced\nSelective Photocatalytic Aerobic Oxidation of Amines into Imines on\nTiO2","volume":"18","author":"Lang","year":"2012","journal-title":"Chem. - Eur. J."},{"key":"2026090118405552000_cit43","doi-asserted-by":"publisher","first-page":"4202","DOI":"10.1039\/C5CY00395D","article-title":"Visible light-induced\nselective photocatalytic aerobic oxidation of amines into imines on\nCu\/graphene","volume":"5","author":"Zhai","year":"2015","journal-title":"Catal. Sci. Technol."},{"key":"2026090118405552000_cit44","doi-asserted-by":"publisher","first-page":"40552","DOI":"10.1039\/C6RA04567G","article-title":"Copper catalyzed\noxidative deamination of Betti bases: an efficient approach for benzoylation\/formylation\nof naphthols and phenols","volume":"6","author":"Deb","year":"2016","journal-title":"RSC Adv."},{"key":"2026090118405552000_cit45","doi-asserted-by":"publisher","first-page":"13481","DOI":"10.1021\/acs.joc.8b02345","article-title":"Aerobic Oxidative\nHomo- and Cross-Coupling of Amines Catalyzed by Phenazine Radical\nCations","volume":"83","author":"Bris\u030car","year":"2018","journal-title":"J. Org. Chem."},{"key":"2026090118405552000_cit46","doi-asserted-by":"publisher","first-page":"3678","DOI":"10.1016\/j.tetlet.2018.08.060","article-title":"B(C6F5)3-catalyzed\noxidative deamination\/cyclization cascade reaction of benzylamines\nand ketones for the synthesis of 2,4,6-triarylpyridines","volume":"59","author":"Ling","year":"2018","journal-title":"Tetrahedron Lett."},{"key":"2026090118405552000_cit47","doi-asserted-by":"publisher","first-page":"10501","DOI":"10.1021\/acs.joc.9b01431","article-title":"Synthetic Access to Secondary Propargylamines via a Copper-Catalyzed\nOxidative Deamination\/Alkynylation Cascade","volume":"84","author":"Li","year":"2019","journal-title":"J. Org. Chem."},{"key":"2026090118405552000_cit48","doi-asserted-by":"publisher","first-page":"122","DOI":"10.1038\/nchem.1536","article-title":"Catalytic transformation\nof alcohols to carboxylic acid salts and H2 using water as the oxygen\natom source","volume":"5","author":"Balaraman","year":"2013","journal-title":"Nat. Chem."},{"key":"2026090118405552000_cit49","doi-asserted-by":"publisher","first-page":"6143","DOI":"10.1021\/jacs.6b03488","article-title":"General Synthesis of Amino Acid Salts\nfrom Amino Alcohols and Basic Water Liberating H2","volume":"138","author":"Hu","year":"2016","journal-title":"J. Am. Chem. Soc."},{"key":"2026090118405552000_cit50","doi-asserted-by":"publisher","first-page":"2998","DOI":"10.1021\/ja500026m","article-title":"Oxidant-Free Conversion of Cyclic\nAmines to Lactams and H2 Using Water As the Oxygen Atom\nSource","volume":"136","author":"Khusnutdinova","year":"2014","journal-title":"J. Am. Chem. Soc."},{"key":"2026090118405552000_cit51","doi-asserted-by":"publisher","first-page":"5980","DOI":"10.1021\/jacs.0c01592","article-title":"Oxidation of Alkenes by Water with\nH2 Liberation","volume":"142","author":"Tang","year":"2020","journal-title":"J. Am. Chem. Soc."},{"key":"2026090118405552000_cit52","doi-asserted-by":"publisher","first-page":"342","DOI":"10.1038\/nchem.1595","article-title":"A homogeneous transition metal complex for clean hydrogen\nproduction from methanol\u2013water mixtures","volume":"5","author":"Rodri\u0301guez-Lugo","year":"2013","journal-title":"Nat. Chem."},{"key":"2026090118405552000_cit53","doi-asserted-by":"publisher","first-page":"12037","DOI":"10.1021\/jacs.6b07411","article-title":"Anti-Markovnikov Oxidation\nof \u03b2-Alkyl Styrenes with H2O as the Terminal Oxidant","volume":"138","author":"Zhang","year":"2016","journal-title":"J. Am. Chem. Soc."},{"key":"2026090118405552000_cit54","doi-asserted-by":"publisher","first-page":"10279","DOI":"10.1021\/jacs.0c03428","article-title":"Enzymatic Primary Amination of Benzylic and Allylic\nC(sp3)\u2013H Bonds","volume":"142","author":"Jia","year":"2020","journal-title":"J. Am. Chem.\nSoc."},{"key":"2026090118405552000_cit55","doi-asserted-by":"publisher","first-page":"3034","DOI":"10.1021\/cs500843a","article-title":"Iridium, Rhodium, and Ruthenium Catalysts\nfor the \u201cAldehyde\u2013Water Shift\u201d Reaction","volume":"4","author":"Brewster","year":"2014","journal-title":"ACS Catal."},{"key":"2026090118405552000_cit56","doi-asserted-by":"publisher","first-page":"6302","DOI":"10.1021\/acscatal.6b02130","article-title":"High Catalytic\nEfficiency Combined with High Selectivity for the Aldehyde\u2013Water\nShift Reaction using (para-cymene)Ruthenium Precatalysts","volume":"6","author":"Brewster","year":"2016","journal-title":"ACS Catal."},{"key":"2026090118405552000_cit57","doi-asserted-by":"publisher","first-page":"6269","DOI":"10.1002\/anie.201301000","article-title":"Direct Deamination\nof Primary Amines\nby Water To Produce Alcohols","volume":"52","author":"Khusnutdinova","year":"2013","journal-title":"Angew. Chem.,\nInt. Ed."},{"key":"2026090118405552000_cit58","doi-asserted-by":"publisher","first-page":"481","DOI":"10.1021\/ar00023a001","article-title":"Recent perspectives concerning the\nmechanism of H3O+- and hydroxide-promoted amide\nhydrolysis","volume":"25","author":"Brown","year":"1992","journal-title":"Acc. Chem. Res."},{"key":"2026090118405552000_cit59","doi-asserted-by":"publisher","first-page":"4851","DOI":"10.1021\/jacs.5b01750","article-title":"Mechanistic Investigations\nof the Catalytic Formation of Lactams from Amines and Water with Liberation\nof H2","volume":"137","author":"Gellrich","year":"2015","journal-title":"J. Am. Chem. Soc."},{"key":"2026090118405552000_cit60","doi-asserted-by":"publisher","first-page":"14763","DOI":"10.1021\/ja107770y","article-title":"Long-Range\u201d\nMetal\u2013Ligand Cooperation in H2 Activation and Ammonia-Promoted\nHydride Transfer with a Ruthenium\u2013Acridine Pincer Complex","volume":"132","author":"Gunanathan","year":"2010","journal-title":"J. Am. Chem. Soc."},{"key":"2026090118405552000_cit61","doi-asserted-by":"publisher","first-page":"5923","DOI":"10.1021\/ja409368a","article-title":"Alcohol Amination with Ammonia Catalyzed by an Acridine-Based\nRuthenium Pincer Complex: A Mechanistic Study","volume":"136","author":"Ye","year":"2014","journal-title":"J. Am. Chem. Soc."},{"key":"2026090118405552000_cit62","doi-asserted-by":"publisher","first-page":"383","DOI":"10.1021\/ja410541v","article-title":"Mechanism of the Formation of Carboxylate from Alcohols\nand Water Catalyzed by a Bipyridine-Based Ruthenium Complex: A Computational\nStudy","volume":"136","author":"Li","year":"2014","journal-title":"J. Am. Chem. 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