Synthesis of 1-Alkyl-3-(2-oxo-2-aryl/alkyl-ethyl)indolin-2-ones through Gold/Bronsted Acid Relay Actions: Observation of Selective C=C Bond Cleavage of Enaminones

Yulei Zhao; Yang Yuan; Lingkai Kong; Fangfang Zhang; Yanzhong Li

doi:10.1055/s-0036-1588820

Synthesis of 1-Alkyl-3-(2-oxo-2-aryl/alkyl-ethyl)indolin-2-ones through Gold/Bronsted Acid Relay Actions: Observation of Selective C=C Bond Cleavage of Enaminones

Yulei Zhao, Yang Yuan, Lingkai Kong, Fangfang Zhang, Yanzhong Li

School of Chemistry and Molecular Engineering

East China Normal University

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

6 Scopus citations

Abstract

A novel gold(I)/Bronsted acid sequential catalyzed/promoted procedure to synthesize 1-alkyl-3-(2-oxo-2-aryl/alkyl-ethyl)indolin-2-ones under mild reaction conditions is developed. This methodology is realized by relay actions of gold and a Bronsted acid in a one-pot multistep manner. The gold(I)-catalyzed chemoselective C(sp ²)-H functionalization of enaminones and Bronsted acid promoted cleavage of the C=C bond are integrated effectively. Based on the results of control experiments and ESI-MS analysis, a possible reaction mechanism is proposed.

Original language	English
Pages (from-to)	3609-3618
Number of pages	10
Journal	Synthesis (Germany)
Volume	49
Issue number	16
DOIs	https://doi.org/10.1055/s-0036-1588820
State	Published - 16 Aug 2017

Keywords

Bronsted acid promotion
C(sp )-H functionalization
carbon-carbon bond activation
gold(I) catalysis
one-pot synthesis

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10.1055/s-0036-1588820

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title = "Synthesis of 1-Alkyl-3-(2-oxo-2-aryl/alkyl-ethyl)indolin-2-ones through Gold/Bronsted Acid Relay Actions: Observation of Selective C=C Bond Cleavage of Enaminones",

abstract = "A novel gold(I)/Bronsted acid sequential catalyzed/promoted procedure to synthesize 1-alkyl-3-(2-oxo-2-aryl/alkyl-ethyl)indolin-2-ones under mild reaction conditions is developed. This methodology is realized by relay actions of gold and a Bronsted acid in a one-pot multistep manner. The gold(I)-catalyzed chemoselective C(sp 2)-H functionalization of enaminones and Bronsted acid promoted cleavage of the C=C bond are integrated effectively. Based on the results of control experiments and ESI-MS analysis, a possible reaction mechanism is proposed.",

keywords = "Bronsted acid promotion, C(sp )-H functionalization, carbon-carbon bond activation, gold(I) catalysis, one-pot synthesis",

author = "Yulei Zhao and Yang Yuan and Lingkai Kong and Fangfang Zhang and Yanzhong Li",

note = "Publisher Copyright: {\textcopyright} Georg Thieme Verlag Stuttgart - New York.",

year = "2017",

month = aug,

day = "16",

doi = "10.1055/s-0036-1588820",

language = "英语",

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TY - JOUR

T1 - Synthesis of 1-Alkyl-3-(2-oxo-2-aryl/alkyl-ethyl)indolin-2-ones through Gold/Bronsted Acid Relay Actions

T2 - Observation of Selective C=C Bond Cleavage of Enaminones

AU - Zhao, Yulei

AU - Yuan, Yang

AU - Kong, Lingkai

AU - Zhang, Fangfang

AU - Li, Yanzhong

N1 - Publisher Copyright: © Georg Thieme Verlag Stuttgart - New York.

PY - 2017/8/16

Y1 - 2017/8/16

N2 - A novel gold(I)/Bronsted acid sequential catalyzed/promoted procedure to synthesize 1-alkyl-3-(2-oxo-2-aryl/alkyl-ethyl)indolin-2-ones under mild reaction conditions is developed. This methodology is realized by relay actions of gold and a Bronsted acid in a one-pot multistep manner. The gold(I)-catalyzed chemoselective C(sp 2)-H functionalization of enaminones and Bronsted acid promoted cleavage of the C=C bond are integrated effectively. Based on the results of control experiments and ESI-MS analysis, a possible reaction mechanism is proposed.

AB - A novel gold(I)/Bronsted acid sequential catalyzed/promoted procedure to synthesize 1-alkyl-3-(2-oxo-2-aryl/alkyl-ethyl)indolin-2-ones under mild reaction conditions is developed. This methodology is realized by relay actions of gold and a Bronsted acid in a one-pot multistep manner. The gold(I)-catalyzed chemoselective C(sp 2)-H functionalization of enaminones and Bronsted acid promoted cleavage of the C=C bond are integrated effectively. Based on the results of control experiments and ESI-MS analysis, a possible reaction mechanism is proposed.

KW - Bronsted acid promotion

KW - C(sp )-H functionalization

KW - carbon-carbon bond activation

KW - gold(I) catalysis

KW - one-pot synthesis

UR - https://www.scopus.com/pages/publications/85019156318

U2 - 10.1055/s-0036-1588820

DO - 10.1055/s-0036-1588820

M3 - 文章

AN - SCOPUS:85019156318

SN - 0039-7881

VL - 49

SP - 3609

EP - 3618

JO - Synthesis (Germany)

JF - Synthesis (Germany)

IS - 16

ER -

Synthesis of 1-Alkyl-3-(2-oxo-2-aryl/alkyl-ethyl)indolin-2-ones through Gold/Bronsted Acid Relay Actions: Observation of Selective C=C Bond Cleavage of Enaminones

Abstract

Keywords

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