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

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

16 Scopus citations

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.

Original language	English
Article number	ss-2015-c0218-st
Pages (from-to)	2924-2930
Number of pages	7
Journal	Synthesis
Volume	47
Issue number	19
DOIs	https://doi.org/10.1055/s-0034-1378718
State	Published - 1 Oct 2015
Externally published	Yes

Keywords

C-C double bond activation
aryl migration
decarboxylation
hypervalent iodine reagents
α-keto diacetates

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10.1055/s-0034-1378718

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

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.",

keywords = "C-C double bond activation, aryl migration, decarboxylation, hypervalent iodine reagents, α-keto diacetates",

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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

U2 - 10.1055/s-0034-1378718

DO - 10.1055/s-0034-1378718

M3 - 文章

AN - SCOPUS:84941941411

SN - 0039-7881

VL - 47

SP - 2924

EP - 2930

JO - Synthesis

JF - Synthesis

IS - 19

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

Abstract

Keywords

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