Photoinduced Intramolecular Haloarylation and Hydroarylation of Alkynes

Dawen Xu; Ramon Rios; Feifei Ba; Dongmei Ma; Guangxin Gu; Aishun Ding; Yunyan Kuang; Hao Guo

doi:10.1002/ajoc.201600232

Photoinduced Intramolecular Haloarylation and Hydroarylation of Alkynes

Dawen Xu
, Ramon Rios
, Feifei Ba
, Dongmei Ma
, Guangxin Gu
, Aishun Ding
, Yunyan Kuang
, Hao Guo

Chemistry

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

12 Scopus citations

Abstract

The cleavage of the aryl C−X bond under UV-irradiation and its subsequent addition into an intramolecular alkyne moiety have been studied carefully. By simply regulating the addition of electron donor, highly chemoselective intramolecular hydroarylation and haloarylation reactions were achieved, providing efficient methods for the synthesis of 9-benzylidene-9H-fluorene and 9-(halo(phenyl)methylene)-9H-fluorene derivatives.

Original language	British English
Pages (from-to)	981-985
Number of pages	5
Journal	Asian Journal of Organic Chemistry
Volume	5
Issue number	8
DOIs	https://doi.org/10.1002/ajoc.201600232
State	Published - 1 Aug 2016

Keywords

haloarylation
hydroarylation
photochemistry
proton transfer
single electron transfer

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10.1002/ajoc.201600232

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title = "Photoinduced Intramolecular Haloarylation and Hydroarylation of Alkynes",

abstract = "The cleavage of the aryl C−X bond under UV-irradiation and its subsequent addition into an intramolecular alkyne moiety have been studied carefully. By simply regulating the addition of electron donor, highly chemoselective intramolecular hydroarylation and haloarylation reactions were achieved, providing efficient methods for the synthesis of 9-benzylidene-9H-fluorene and 9-(halo(phenyl)methylene)-9H-fluorene derivatives.",

keywords = "haloarylation, hydroarylation, photochemistry, proton transfer, single electron transfer",

author = "Dawen Xu and Ramon Rios and Feifei Ba and Dongmei Ma and Guangxin Gu and Aishun Ding and Yunyan Kuang and Hao Guo",

note = "Publisher Copyright: {\textcopyright} 2016 WILEY-VCH Verlag GmbH \& Co. KGaA, Weinheim",

year = "2016",

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doi = "10.1002/ajoc.201600232",

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TY - JOUR

T1 - Photoinduced Intramolecular Haloarylation and Hydroarylation of Alkynes

AU - Xu, Dawen

AU - Rios, Ramon

AU - Ba, Feifei

AU - Ma, Dongmei

AU - Gu, Guangxin

AU - Ding, Aishun

AU - Kuang, Yunyan

AU - Guo, Hao

PY - 2016/8/1

Y1 - 2016/8/1

N2 - The cleavage of the aryl C−X bond under UV-irradiation and its subsequent addition into an intramolecular alkyne moiety have been studied carefully. By simply regulating the addition of electron donor, highly chemoselective intramolecular hydroarylation and haloarylation reactions were achieved, providing efficient methods for the synthesis of 9-benzylidene-9H-fluorene and 9-(halo(phenyl)methylene)-9H-fluorene derivatives.

AB - The cleavage of the aryl C−X bond under UV-irradiation and its subsequent addition into an intramolecular alkyne moiety have been studied carefully. By simply regulating the addition of electron donor, highly chemoselective intramolecular hydroarylation and haloarylation reactions were achieved, providing efficient methods for the synthesis of 9-benzylidene-9H-fluorene and 9-(halo(phenyl)methylene)-9H-fluorene derivatives.

KW - haloarylation

KW - hydroarylation

KW - photochemistry

KW - proton transfer

KW - single electron transfer

UR - https://www.scopus.com/pages/publications/84981276060

U2 - 10.1002/ajoc.201600232

DO - 10.1002/ajoc.201600232

M3 - Article

AN - SCOPUS:84981276060

SN - 2193-5807

VL - 5

SP - 981

EP - 985

JO - Asian Journal of Organic Chemistry

JF - Asian Journal of Organic Chemistry

IS - 8

ER -

Photoinduced Intramolecular Haloarylation and Hydroarylation of Alkynes

Abstract

Keywords

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