Literature DB >> 27934459

Electrochemically Oxidative α-C-H Functionalization of Ketones: A Cascade Synthesis of α-Amino Ketones Mediated by NH4I.

Sen Liang1,2, Cheng-Chu Zeng1,3, Hong-Yu Tian1, Bao-Guo Sun1, Xu-Gang Luo2, Fa-Zheng Ren2.   

Abstract

An efficient electrochemical protocol for the synthesis of α-amino ketones via the oxidative cross-dehydrogenative coupling of ketones and secondary amines has been developed. The electrochemistry performs in a simple undivided cell using NH4I as a redox catalyst and a cheap graphite plate as electrodes under constant current conditions. Gram-scale reaction demonstrates the practicality of the protocol. The reaction is proposed to procced through an initial α-iodination of ketone, followed by a nucleophilic substitution of amines.

Entities:  

Year:  2016        PMID: 27934459     DOI: 10.1021/acs.joc.6b01595

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  3 in total

1.  Merging Photochemistry with Electrochemistry: Functional-Group Tolerant Electrochemical Amination of C(sp3 )-H Bonds.

Authors:  Fei Wang; Shannon S Stahl
Journal:  Angew Chem Int Ed Engl       Date:  2019-03-14       Impact factor: 15.336

2.  Synthetic Organic Electrochemical Methods Since 2000: On the Verge of a Renaissance.

Authors:  Ming Yan; Yu Kawamata; Phil S Baran
Journal:  Chem Rev       Date:  2017-10-09       Impact factor: 60.622

3.  A one-pot electrochemical synthesis of 2-aminothiazoles from active methylene ketones and thioureas mediated by NH4I.

Authors:  Shang-Feng Yang; Pei Li; Zi-Lin Fang; Sen Liang; Hong-Yu Tian; Bao-Guo Sun; Kun Xu; Cheng-Chu Zeng
Journal:  Beilstein J Org Chem       Date:  2022-09-15       Impact factor: 2.544

  3 in total

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