Hypervalent Iodine Mediated C-C Double Bond Activation: A Cascade Access to α-Keto Diacetates from Readily Available Cinnamic Acids

Le Liu; Daisy Zhang-Negrerie; Yunfei Du; Kang Zhao

doi:10.1055/s-0034-1378718

Hypervalent Iodine Mediated C-C Double Bond Activation: A Cascade Access to α-Keto Diacetates from Readily Available Cinnamic Acids

Le Liu
, Daisy Zhang-Negrerie
, Yunfei Du
, Kang Zhao

Tianjin University

科研成果: 期刊稿件 › 文章 › 同行评审

16 引用（Scopus）

摘要

The reaction of cinnamic acids with (diacetoxyiodo)benzene in 1,2-dichloroethane in the presence of sulfuric acid provides an easy and direct access to the α-keto diacetate framework. This hypervalent iodine mediated oxidative reaction involves a tandem sequence of aryl migration, insertion of an oxygen atom, decarboxylation and diacetoxylation. A reaction mechanism is proposed and discussed in light of control experiments.

源语言	英语
文章编号	ss-2015-c0218-st
页（从-至）	2924-2930
页数	7
期刊	Synthesis
卷	47
期	19
DOI	https://doi.org/10.1055/s-0034-1378718
出版状态	已出版 - 1 10月 2015
已对外发布	是

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abstract = "The reaction of cinnamic acids with (diacetoxyiodo)benzene in 1,2-dichloroethane in the presence of sulfuric acid provides an easy and direct access to the α-keto diacetate framework. This hypervalent iodine mediated oxidative reaction involves a tandem sequence of aryl migration, insertion of an oxygen atom, decarboxylation and diacetoxylation. A reaction mechanism is proposed and discussed in light of control experiments.",

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T2 - A Cascade Access to α-Keto Diacetates from Readily Available Cinnamic Acids

AU - Liu, Le

AU - Zhang-Negrerie, Daisy

AU - Du, Yunfei

AU - Zhao, Kang

PY - 2015/10/1

Y1 - 2015/10/1

N2 - The reaction of cinnamic acids with (diacetoxyiodo)benzene in 1,2-dichloroethane in the presence of sulfuric acid provides an easy and direct access to the α-keto diacetate framework. This hypervalent iodine mediated oxidative reaction involves a tandem sequence of aryl migration, insertion of an oxygen atom, decarboxylation and diacetoxylation. A reaction mechanism is proposed and discussed in light of control experiments.

AB - The reaction of cinnamic acids with (diacetoxyiodo)benzene in 1,2-dichloroethane in the presence of sulfuric acid provides an easy and direct access to the α-keto diacetate framework. This hypervalent iodine mediated oxidative reaction involves a tandem sequence of aryl migration, insertion of an oxygen atom, decarboxylation and diacetoxylation. A reaction mechanism is proposed and discussed in light of control experiments.

KW - C-C double bond activation

KW - aryl migration

KW - decarboxylation

KW - hypervalent iodine reagents

KW - α-keto diacetates

UR - https://www.scopus.com/pages/publications/84941941411

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JO - Synthesis

JF - Synthesis

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M1 - ss-2015-c0218-st

ER -

Hypervalent Iodine Mediated C-C Double Bond Activation: A Cascade Access to α-Keto Diacetates from Readily Available Cinnamic Acids

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