Metal-free tandem oxidative aryl migration and C-C bond cleavage: Synthesis of α-ketoamides and esters from acrylic derivatives

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

doi:10.1021/ol502834g

Metal-free tandem oxidative aryl migration and C-C bond cleavage: Synthesis of α-ketoamides and esters from acrylic derivatives

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

Tianjin University
Collaborative Innovative Centre of Chemical Science and Engineering (Tianjin)

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

68 Scopus citations

Abstract

A novel tandem metal-free oxidative aryl migration/C-C bond-cleavage reaction, mediated by hypervalent iodine reagent, has been discovered. The presented transformation provided straightforward access to important α-ketoamide and α-ketoester derivatives from readily available acrylic derivatives via a concerted process of 1,2-aryl shift concomitant with C-C bond cleavage.

Original language	English
Pages (from-to)	5772-5775
Number of pages	4
Journal	Organic Letters
Volume	16
Issue number	21
DOIs	https://doi.org/10.1021/ol502834g
State	Published - 7 Nov 2014
Externally published	Yes

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10.1021/ol502834g

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title = "Metal-free tandem oxidative aryl migration and C-C bond cleavage: Synthesis of α-ketoamides and esters from acrylic derivatives",

abstract = "A novel tandem metal-free oxidative aryl migration/C-C bond-cleavage reaction, mediated by hypervalent iodine reagent, has been discovered. The presented transformation provided straightforward access to important α-ketoamide and α-ketoester derivatives from readily available acrylic derivatives via a concerted process of 1,2-aryl shift concomitant with C-C bond cleavage.",

author = "Le Liu and Liang Du and Daisy Zhang-Negrerie and Yunfei Du and Kang Zhao",

note = "Publisher Copyright: {\textcopyright} 2014 American Chemical Society.",

year = "2014",

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doi = "10.1021/ol502834g",

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journal = "Organic Letters",

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T2 - Synthesis of α-ketoamides and esters from acrylic derivatives

AU - Liu, Le

AU - Du, Liang

AU - Zhang-Negrerie, Daisy

AU - Du, Yunfei

AU - Zhao, Kang

PY - 2014/11/7

Y1 - 2014/11/7

N2 - A novel tandem metal-free oxidative aryl migration/C-C bond-cleavage reaction, mediated by hypervalent iodine reagent, has been discovered. The presented transformation provided straightforward access to important α-ketoamide and α-ketoester derivatives from readily available acrylic derivatives via a concerted process of 1,2-aryl shift concomitant with C-C bond cleavage.

AB - A novel tandem metal-free oxidative aryl migration/C-C bond-cleavage reaction, mediated by hypervalent iodine reagent, has been discovered. The presented transformation provided straightforward access to important α-ketoamide and α-ketoester derivatives from readily available acrylic derivatives via a concerted process of 1,2-aryl shift concomitant with C-C bond cleavage.

UR - https://www.scopus.com/pages/publications/84909999896

U2 - 10.1021/ol502834g

DO - 10.1021/ol502834g

M3 - 文章

C2 - 25343425

AN - SCOPUS:84909999896

SN - 1523-7060

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EP - 5775

JO - Organic Letters

JF - Organic Letters

IS - 21

ER -

Metal-free tandem oxidative aryl migration and C-C bond cleavage: Synthesis of α-ketoamides and esters from acrylic derivatives

Abstract

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