Metal-Free Oxidative Decarboxylative Acylation/Ring Expansion of Vinylcyclobutanols with α-Keto Acids by Visible Light Photoredox Catalysis

Jin Jiang Zhang; Yuan Bo Cheng; Xin Hua Duan

doi:10.1002/cjoc.201600729

Metal-Free Oxidative Decarboxylative Acylation/Ring Expansion of Vinylcyclobutanols with α-Keto Acids by Visible Light Photoredox Catalysis

Jin Jiang Zhang
, Yuan Bo Cheng
, Xin Hua Duan

School of Chemistry

Xi'an Jiaotong University

Research output: Contribution to journal › Article › peer-review

72 Scopus citations

Abstract

A metal-free visible-light-mediated decarboxylative acylation/ring expansion of vinylcyclobutanols with α-keto acids has been developed. Hypervalent iodine reagent was found to be important for promoting decarboxylation of α-keto acids in this tandem radical process. This protocol has been successfully applied to synthesis of a variety of substituted 1,4-dicarbonyl compounds and tolerated some functional groups well.

Original language	English
Pages (from-to)	311-315
Number of pages	5
Journal	Chinese Journal of Chemistry
Volume	35
Issue number	3
DOIs	https://doi.org/10.1002/cjoc.201600729
State	Published - Mar 2017

Keywords

oxidative decarboxylation
radical
visible light
α-keto acids

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10.1002/cjoc.201600729

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title = "Metal-Free Oxidative Decarboxylative Acylation/Ring Expansion of Vinylcyclobutanols with α-Keto Acids by Visible Light Photoredox Catalysis",

abstract = "A metal-free visible-light-mediated decarboxylative acylation/ring expansion of vinylcyclobutanols with α-keto acids has been developed. Hypervalent iodine reagent was found to be important for promoting decarboxylation of α-keto acids in this tandem radical process. This protocol has been successfully applied to synthesis of a variety of substituted 1,4-dicarbonyl compounds and tolerated some functional groups well.",

keywords = "oxidative decarboxylation, radical, visible light, α-keto acids",

author = "Zhang, \{Jin Jiang\} and Cheng, \{Yuan Bo\} and Duan, \{Xin Hua\}",

note = "Publisher Copyright: {\textcopyright} 2017 SIOC, CAS, Shanghai, \& WILEY-VCH Verlag GmbH \& Co. KGaA, Weinheim",

year = "2017",

month = mar,

doi = "10.1002/cjoc.201600729",

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volume = "35",

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journal = "Chinese Journal of Chemistry",

issn = "1001-604X",

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T1 - Metal-Free Oxidative Decarboxylative Acylation/Ring Expansion of Vinylcyclobutanols with α-Keto Acids by Visible Light Photoredox Catalysis

AU - Zhang, Jin Jiang

AU - Cheng, Yuan Bo

AU - Duan, Xin Hua

PY - 2017/3

Y1 - 2017/3

N2 - A metal-free visible-light-mediated decarboxylative acylation/ring expansion of vinylcyclobutanols with α-keto acids has been developed. Hypervalent iodine reagent was found to be important for promoting decarboxylation of α-keto acids in this tandem radical process. This protocol has been successfully applied to synthesis of a variety of substituted 1,4-dicarbonyl compounds and tolerated some functional groups well.

AB - A metal-free visible-light-mediated decarboxylative acylation/ring expansion of vinylcyclobutanols with α-keto acids has been developed. Hypervalent iodine reagent was found to be important for promoting decarboxylation of α-keto acids in this tandem radical process. This protocol has been successfully applied to synthesis of a variety of substituted 1,4-dicarbonyl compounds and tolerated some functional groups well.

KW - oxidative decarboxylation

KW - radical

KW - visible light

KW - α-keto acids

UR - https://www.scopus.com/pages/publications/85013900553

U2 - 10.1002/cjoc.201600729

DO - 10.1002/cjoc.201600729

M3 - 文章

AN - SCOPUS:85013900553

SN - 1001-604X

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SP - 311

EP - 315

JO - Chinese Journal of Chemistry

JF - Chinese Journal of Chemistry

IS - 3

ER -

Metal-Free Oxidative Decarboxylative Acylation/Ring Expansion of Vinylcyclobutanols with α-Keto Acids by Visible Light Photoredox Catalysis

Abstract

Keywords

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