Literature DB >> 24521458

Oxidant-free conversion of cyclic amines to lactams and H2 using water as the oxygen atom source.

Julia R Khusnutdinova1, Yehoshoa Ben-David, David Milstein.   

Abstract

Direct conversion of cyclic amines to lactams utilizing water as the only reagent is catalyzed by pincer complex 2. In contrast to previously known methods of amine-to-amide conversion, this reaction occurs in the absence of oxidants and is accompanied by liberation of H2, with water serving as a source of oxygen atom. Formation of a cyclic hemiaminal intermediate plays a key role in enabling such reactivity. This represents an unprecedented, conceptually new type of amide formation reaction directly from amines and water under oxidant-free conditions.

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Year:  2014        PMID: 24521458     DOI: 10.1021/ja500026m

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  10 in total

1.  Facile synthesis of amides via acceptorless dehydrogenative coupling of aryl epoxides and amines.

Authors:  Yaoyu Liang; Jie Luo; David Milstein
Journal:  Chem Sci       Date:  2022-04-26       Impact factor: 9.969

2.  Iron-Catalyzed Oxyfunctionalization of Aliphatic Amines at Remote Benzylic C-H Sites.

Authors:  Curren T Mbofana; Eugene Chong; James Lawniczak; Melanie S Sanford
Journal:  Org Lett       Date:  2016-08-16       Impact factor: 6.005

3.  Reaction-activated palladium catalyst for dehydrogenation of substituted cyclohexanones to phenols and H2 without oxidants and hydrogen acceptors.

Authors:  Jingwu Zhang; Qiangqiang Jiang; Dejun Yang; Xiaomei Zhao; Yanli Dong; Renhua Liu
Journal:  Chem Sci       Date:  2015-05-19       Impact factor: 9.825

4.  Catalytic Oxidative Deamination by Water with H2 Liberation.

Authors:  Shan Tang; Michael Rauch; Michael Montag; Yael Diskin-Posner; Yehoshoa Ben-David; David Milstein
Journal:  J Am Chem Soc       Date:  2020-11-25       Impact factor: 15.419

5.  Dehydrogenative ester synthesis from enol ethers and water with a ruthenium complex catalyzing two reactions in synergy.

Authors:  Sayan Kar; Jie Luo; Michael Rauch; Yael Diskin-Posner; Yehoshoa Ben-David; David Milstein
Journal:  Green Chem       Date:  2022-02-04       Impact factor: 10.182

Review 6.  Sustainable catalysis with fluxional acridine-based PNP pincer complexes.

Authors:  Sayan Kar; David Milstein
Journal:  Chem Commun (Camb)       Date:  2022-03-18       Impact factor: 6.222

7.  Synthesis of heteroatom-containing pyrrolidine derivatives based on Ti(O-iPr)4 and EtMgBr-catalyzed carbocyclization of allylpropargyl amines with Et2Zn.

Authors:  Rita N Kadikova; Ilfir R Ramazanov; Azat M Gabdullin; Oleg S Mozgovoj; Usein M Dzhemilev
Journal:  RSC Adv       Date:  2020-05-07       Impact factor: 4.036

8.  Oxidation of Organic Compounds Using Water as the Oxidant with H2 Liberation Catalyzed by Molecular Metal Complexes.

Authors:  Sayan Kar; David Milstein
Journal:  Acc Chem Res       Date:  2022-07-26       Impact factor: 24.466

9.  Rhodium-catalyzed oxidative amidation of allylic alcohols and aldehydes: effective conversion of amines and anilines into amides.

Authors:  Zhao Wu; Kami L Hull
Journal:  Chem Sci       Date:  2015-10-27       Impact factor: 9.825

10.  Glaulactams A-C, daphniphyllum alkaloids from Daphniphyllum glaucescens.

Authors:  Chih-Hua Chao; Ju-Chien Cheng; Théo P Gonçalves; Kuo-Wei Huang; Chi-Chien Lin; Hui-Chi Huang; Syh-Yuan Hwang; Yang-Chang Wu
Journal:  Sci Rep       Date:  2018-10-18       Impact factor: 4.379

  10 in total

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