Directed palladium(II)-catalyzed intermolecular anti-markovnikov hydroarylation of unactivated alkenes with (hetero)arylsilanes

Ming Zhu Lu; Teck Peng Loh; Haiqing Luo; Zhengsong Hu; Changdong Shao; Yuhe Kan

doi:10.1021/acs.orglett.0c03416

Directed palladium(II)-catalyzed intermolecular anti-markovnikov hydroarylation of unactivated alkenes with (hetero)arylsilanes

Ming Zhu Lu, Teck Peng Loh, Haiqing Luo, Zhengsong Hu, Changdong Shao, Yuhe Kan

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

15 Scopus citations

Abstract

We describe herein a regioselective palladium(II)catalyzed intermolecular hydroarylation of unactivated aliphatic alkenes with electronically and sterically diverse (hetero)arylsilanes under redox-neutral conditions. A removable bidentate 8-amino-quinoline auxiliary was readily employed to dictate the regioselectivity, prevent β-hydride elimination, and facilitate protodepalladation. This silicon-based protocol features a broad substrate scope with excellent functional group compatibility and enables an expeditious route to a variety of γ-aryl butyric acid derivatives in good yields with exclusive anti-Markovnikov selectivity.

Original language	English
Pages (from-to)	9022-9028
Number of pages	7
Journal	Organic Letters
Volume	22
Issue number	22
DOIs	https://doi.org/10.1021/acs.orglett.0c03416
State	Published - 20 Nov 2020
Externally published	Yes

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abstract = "We describe herein a regioselective palladium(II)catalyzed intermolecular hydroarylation of unactivated aliphatic alkenes with electronically and sterically diverse (hetero)arylsilanes under redox-neutral conditions. A removable bidentate 8-amino-quinoline auxiliary was readily employed to dictate the regioselectivity, prevent β-hydride elimination, and facilitate protodepalladation. This silicon-based protocol features a broad substrate scope with excellent functional group compatibility and enables an expeditious route to a variety of γ-aryl butyric acid derivatives in good yields with exclusive anti-Markovnikov selectivity.",

author = "Lu, {Ming Zhu} and Loh, {Teck Peng} and Haiqing Luo and Zhengsong Hu and Changdong Shao and Yuhe Kan",

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T1 - Directed palladium(II)-catalyzed intermolecular anti-markovnikov hydroarylation of unactivated alkenes with (hetero)arylsilanes

AU - Lu, Ming Zhu

AU - Loh, Teck Peng

AU - Luo, Haiqing

AU - Hu, Zhengsong

AU - Shao, Changdong

AU - Kan, Yuhe

PY - 2020/11/20

Y1 - 2020/11/20

N2 - We describe herein a regioselective palladium(II)catalyzed intermolecular hydroarylation of unactivated aliphatic alkenes with electronically and sterically diverse (hetero)arylsilanes under redox-neutral conditions. A removable bidentate 8-amino-quinoline auxiliary was readily employed to dictate the regioselectivity, prevent β-hydride elimination, and facilitate protodepalladation. This silicon-based protocol features a broad substrate scope with excellent functional group compatibility and enables an expeditious route to a variety of γ-aryl butyric acid derivatives in good yields with exclusive anti-Markovnikov selectivity.

AB - We describe herein a regioselective palladium(II)catalyzed intermolecular hydroarylation of unactivated aliphatic alkenes with electronically and sterically diverse (hetero)arylsilanes under redox-neutral conditions. A removable bidentate 8-amino-quinoline auxiliary was readily employed to dictate the regioselectivity, prevent β-hydride elimination, and facilitate protodepalladation. This silicon-based protocol features a broad substrate scope with excellent functional group compatibility and enables an expeditious route to a variety of γ-aryl butyric acid derivatives in good yields with exclusive anti-Markovnikov selectivity.

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DO - 10.1021/acs.orglett.0c03416

M3 - 文章

C2 - 33151076

AN - SCOPUS:85096509174

SN - 1523-7060

VL - 22

SP - 9022

EP - 9028

JO - Organic Letters

JF - Organic Letters

IS - 22

ER -

Directed palladium(II)-catalyzed intermolecular anti-markovnikov hydroarylation of unactivated alkenes with (hetero)arylsilanes

Abstract

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