Regioselective and Geometrically Controlled Heck 1,1-Diarylation of Unactivated Aliphatic Alkenes

Yao Zhao; Shuangqiang Wang; Huihui Shao; Xuyong Tan; Rizhi Chen; Teck Peng Loh; Jianrong Steve Zhou; Xiaojin Wu

doi:10.1021/acs.orglett.3c01214

Regioselective and Geometrically Controlled Heck 1,1-Diarylation of Unactivated Aliphatic Alkenes

Yao Zhao, Shuangqiang Wang, Huihui Shao, Xuyong Tan, Rizhi Chen, Teck Peng Loh, Jianrong Steve Zhou, Xiaojin Wu^*

^*Corresponding author for this work

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

6 Citations (Scopus)

Abstract

Pd-catalyzed double Heck reaction allows regioselective 1,1-diarylation of unactivated aliphatic alkenes. When two different aryl bromides are used, the second aryl rings are added trans to aliphatic chains in the main olefinic isomers, consistent with a mechanism of two consecutive Heck arylations at the terminal carbons.

Original language	English
Pages (from-to)	4258-4263
Number of pages	6
Journal	Organic Letters
Volume	25
Issue number	23
DOIs	https://doi.org/10.1021/acs.orglett.3c01214
Publication status	Published - Jun 16 2023
Externally published	Yes

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© 2023 American Chemical Society. All rights reserved.

ASJC Scopus Subject Areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.3c01214

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title = "Regioselective and Geometrically Controlled Heck 1,1-Diarylation of Unactivated Aliphatic Alkenes",

abstract = "Pd-catalyzed double Heck reaction allows regioselective 1,1-diarylation of unactivated aliphatic alkenes. When two different aryl bromides are used, the second aryl rings are added trans to aliphatic chains in the main olefinic isomers, consistent with a mechanism of two consecutive Heck arylations at the terminal carbons.",

author = "Yao Zhao and Shuangqiang Wang and Huihui Shao and Xuyong Tan and Rizhi Chen and Loh, \{Teck Peng\} and Zhou, \{Jianrong Steve\} and Xiaojin Wu",

year = "2023",

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doi = "10.1021/acs.orglett.3c01214",

language = "English",

volume = "25",

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journal = "Organic Letters",

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T1 - Regioselective and Geometrically Controlled Heck 1,1-Diarylation of Unactivated Aliphatic Alkenes

AU - Zhao, Yao

AU - Wang, Shuangqiang

AU - Shao, Huihui

AU - Tan, Xuyong

AU - Chen, Rizhi

AU - Loh, Teck Peng

AU - Zhou, Jianrong Steve

AU - Wu, Xiaojin

PY - 2023/6/16

Y1 - 2023/6/16

N2 - Pd-catalyzed double Heck reaction allows regioselective 1,1-diarylation of unactivated aliphatic alkenes. When two different aryl bromides are used, the second aryl rings are added trans to aliphatic chains in the main olefinic isomers, consistent with a mechanism of two consecutive Heck arylations at the terminal carbons.

AB - Pd-catalyzed double Heck reaction allows regioselective 1,1-diarylation of unactivated aliphatic alkenes. When two different aryl bromides are used, the second aryl rings are added trans to aliphatic chains in the main olefinic isomers, consistent with a mechanism of two consecutive Heck arylations at the terminal carbons.

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U2 - 10.1021/acs.orglett.3c01214

DO - 10.1021/acs.orglett.3c01214

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JO - Organic Letters

JF - Organic Letters

IS - 23

ER -

Regioselective and Geometrically Controlled Heck 1,1-Diarylation of Unactivated Aliphatic Alkenes

Abstract

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ASJC Scopus Subject Areas

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