Iminyl Radical-Mediated Controlled Hydroxyalkylation of Remote C(sp3)-H Bond via Tandem 1,5-HAT and Difunctionalization of Aryl Alkenes

Zhi Yong Ma; Li Na Guo; Yu Rui Gu; Li Chen; Xin Hua Duan

doi:10.1002/adsc.201801198

Iminyl Radical-Mediated Controlled Hydroxyalkylation of Remote C(sp³)-H Bond via Tandem 1,5-HAT and Difunctionalization of Aryl Alkenes

Zhi Yong Ma
, Li Na Guo
, Yu Rui Gu
, Li Chen
, Xin Hua Duan

School of Chemistry

Xi'an Jiaotong University

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

45 Scopus citations

Abstract

A visible-light mediated γ-hydroxyalkylation of ketones via C(sp³)-H functionalization has been developed under redox neutral conditions. This protocol relies on the iminyl radical-triggered 1,5-HAT followed by oxyalkylation of alkenes, wherein C−C and C−O bonds were constructed in one step. This three-component reaction features mild conditions, wide substrate scope and excellent functional group tolerance, thus providing a facile and highly efficient access to complex valuable ketones. (Figure presented.).

Original language	English
Pages (from-to)	4341-4347
Number of pages	7
Journal	Advanced Synthesis and Catalysis
Volume	360
Issue number	22
DOIs	https://doi.org/10.1002/adsc.201801198
State	Published - 16 Nov 2018

Keywords

1,5-HAT
difunctionalization
iminyl radical
multicomponent reactions
γ C−H functionalization

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10.1002/adsc.201801198

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title = "Iminyl Radical-Mediated Controlled Hydroxyalkylation of Remote C(sp3)-H Bond via Tandem 1,5-HAT and Difunctionalization of Aryl Alkenes",

abstract = "A visible-light mediated γ-hydroxyalkylation of ketones via C(sp3)-H functionalization has been developed under redox neutral conditions. This protocol relies on the iminyl radical-triggered 1,5-HAT followed by oxyalkylation of alkenes, wherein C−C and C−O bonds were constructed in one step. This three-component reaction features mild conditions, wide substrate scope and excellent functional group tolerance, thus providing a facile and highly efficient access to complex valuable ketones. (Figure presented.).",

keywords = "1,5-HAT, difunctionalization, iminyl radical, multicomponent reactions, γ C−H functionalization",

author = "Ma, \{Zhi Yong\} and Guo, \{Li Na\} and Gu, \{Yu Rui\} and Li Chen and Duan, \{Xin Hua\}",

note = "Publisher Copyright: {\textcopyright} 2018 Wiley-VCH Verlag GmbH \& Co. KGaA, Weinheim",

year = "2018",

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T1 - Iminyl Radical-Mediated Controlled Hydroxyalkylation of Remote C(sp3)-H Bond via Tandem 1,5-HAT and Difunctionalization of Aryl Alkenes

AU - Ma, Zhi Yong

AU - Guo, Li Na

AU - Gu, Yu Rui

AU - Chen, Li

AU - Duan, Xin Hua

PY - 2018/11/16

Y1 - 2018/11/16

N2 - A visible-light mediated γ-hydroxyalkylation of ketones via C(sp3)-H functionalization has been developed under redox neutral conditions. This protocol relies on the iminyl radical-triggered 1,5-HAT followed by oxyalkylation of alkenes, wherein C−C and C−O bonds were constructed in one step. This three-component reaction features mild conditions, wide substrate scope and excellent functional group tolerance, thus providing a facile and highly efficient access to complex valuable ketones. (Figure presented.).

AB - A visible-light mediated γ-hydroxyalkylation of ketones via C(sp3)-H functionalization has been developed under redox neutral conditions. This protocol relies on the iminyl radical-triggered 1,5-HAT followed by oxyalkylation of alkenes, wherein C−C and C−O bonds were constructed in one step. This three-component reaction features mild conditions, wide substrate scope and excellent functional group tolerance, thus providing a facile and highly efficient access to complex valuable ketones. (Figure presented.).

KW - 1,5-HAT

KW - difunctionalization

KW - iminyl radical

KW - multicomponent reactions

KW - γ C−H functionalization

UR - https://www.scopus.com/pages/publications/85054784132

U2 - 10.1002/adsc.201801198

DO - 10.1002/adsc.201801198

M3 - 文章

AN - SCOPUS:85054784132

SN - 1615-4150

VL - 360

SP - 4341

EP - 4347

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

IS - 22

ER -

Iminyl Radical-Mediated Controlled Hydroxyalkylation of Remote C(sp³)-H Bond via Tandem 1,5-HAT and Difunctionalization of Aryl Alkenes

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Keywords

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