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Rh(III)-Catalyzed Redox-Neutral Unsymmetrical C-H Alkylation and Amidation Reactions of N-Phenoxyacetamides.

A Rh(III)-catalyzed unsymmetrical C-H alkylation and amidation of N-phenoxyacetamides with diazo compounds has been developed under mild and redox-neutral conditions, producing dinitrogen as the only byproduct. The reaction represents the first example of one-step, unsymmetrical difunctionalization... Full description

Journal Title: Journal of the American Chemical Society January 10, 2018, Vol.140(1), pp.42-45
Main Author: Wu, Yunxiang
Other Authors: Chen, Zhaoqiang , Yang, Yaxi , Zhu, Weiliang , Zhou, Bing
Format: Electronic Article Electronic Article
Language: English
ID: E-ISSN: 1520-5126 ; DOI: 10.1021/jacs.7b10349
Link: http://search.proquest.com/docview/1966244879/?pq-origsite=primo
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title: Rh(III)-Catalyzed Redox-Neutral Unsymmetrical C-H Alkylation and Amidation Reactions of N-Phenoxyacetamides.
format: Article
creator:
  • Wu, Yunxiang
  • Chen, Zhaoqiang
  • Yang, Yaxi
  • Zhu, Weiliang
  • Zhou, Bing
ispartof: Journal of the American Chemical Society, January 10, 2018, Vol.140(1), pp.42-45
description: A Rh(III)-catalyzed unsymmetrical C-H alkylation and amidation of N-phenoxyacetamides with diazo compounds has been developed under mild and redox-neutral conditions, producing dinitrogen as the only byproduct. The reaction represents the first example of one-step, unsymmetrical difunctionalization of two ortho-C-H bonds. Experimental and computational studies support that N-phenoxyacetamides most likely undergo an initial ortho-C-H alkylation with diazo compounds via a Rh(III)-catalyzed C-H activation, and the resulting Rh(III) intermediate subsequently undergoes an intramolecular oxidative addition into the O-N bond to form a Rh(V) nitrenoid species that is protonated and further directed toward electrophilic addition to the second ortho position of the phenyl ring. This work might provide a new direction for unsymmetrical C-H difunctionalization reactions in an efficient manner.
language: eng
source:
identifier: E-ISSN: 1520-5126 ; DOI: 10.1021/jacs.7b10349
fulltext: fulltext
issn:
  • 15205126
  • 1520-5126
url: Link


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descriptionA Rh(III)-catalyzed unsymmetrical C-H alkylation and amidation of N-phenoxyacetamides with diazo compounds has been developed under mild and redox-neutral conditions, producing dinitrogen as the only byproduct. The reaction represents the first example of one-step, unsymmetrical difunctionalization of two ortho-C-H bonds. Experimental and computational studies support that N-phenoxyacetamides most likely undergo an initial ortho-C-H alkylation with diazo compounds via a Rh(III)-catalyzed C-H activation, and the resulting Rh(III) intermediate subsequently undergoes an intramolecular oxidative addition into the O-N bond to form a Rh(V) nitrenoid species that is protonated and further directed toward electrophilic addition to the second ortho position of the phenyl ring. This work might provide a new direction for unsymmetrical C-H difunctionalization reactions in an efficient manner.
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