Nickel-Catalyzed Regioselective Intermolecular Dialkylation of Alkenylarenes: Generation of Two Vicinal C(sp3)−C(sp3) Bonds Across Alkenes**

Daniel M. Lux; Vivek Aryal; Doleshwar Niroula; Ramesh Giri

doi:10.1002/anie.202305522

Nickel-Catalyzed Regioselective Intermolecular Dialkylation of Alkenylarenes: Generation of Two Vicinal C(sp³)−C(sp³) Bonds Across Alkenes**

Daniel M. Lux
, Vivek Aryal
, Doleshwar Niroula
, Ramesh Giri

Chemistry

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

20 Scopus citations

Abstract

We disclose a Ni-catalyzed regioselective dialkylation reaction of alkenylarenes with α-halocarbonyls and alkylzinc reagents. The reaction produces γ-arylated alkanecarbonyl compounds with the generation of two new C(sp³)−C(sp³) bonds at the vicinal carbons of alkenes. This reaction is effective for the use of primary, secondary and tertiary α-halocarboxylic esters, amides and ketones in conjunction with primary and secondary alkylzinc reagents as the sources of two C(sp³) carbons for the dialkylation of terminal and cyclic internal alkenes.

Original language	English (US)
Article number	e202305522
Journal	Angewandte Chemie - International Edition
Volume	62
Issue number	32
DOIs	https://doi.org/10.1002/anie.202305522
State	Published - Aug 7 2023

All Science Journal Classification (ASJC) codes

Catalysis
General Chemistry

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10.1002/anie.202305522

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title = "Nickel-Catalyzed Regioselective Intermolecular Dialkylation of Alkenylarenes: Generation of Two Vicinal C(sp3)−C(sp3) Bonds Across Alkenes**",

abstract = "We disclose a Ni-catalyzed regioselective dialkylation reaction of alkenylarenes with α-halocarbonyls and alkylzinc reagents. The reaction produces γ-arylated alkanecarbonyl compounds with the generation of two new C(sp3)−C(sp3) bonds at the vicinal carbons of alkenes. This reaction is effective for the use of primary, secondary and tertiary α-halocarboxylic esters, amides and ketones in conjunction with primary and secondary alkylzinc reagents as the sources of two C(sp3) carbons for the dialkylation of terminal and cyclic internal alkenes.",

author = "Lux, \{Daniel M.\} and Vivek Aryal and Doleshwar Niroula and Ramesh Giri",

note = "Publisher Copyright: {\textcopyright} 2023 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.",

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doi = "10.1002/anie.202305522",

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TY - JOUR

T1 - Nickel-Catalyzed Regioselective Intermolecular Dialkylation of Alkenylarenes

T2 - Generation of Two Vicinal C(sp3)−C(sp3) Bonds Across Alkenes**

AU - Lux, Daniel M.

AU - Aryal, Vivek

AU - Niroula, Doleshwar

AU - Giri, Ramesh

PY - 2023/8/7

Y1 - 2023/8/7

N2 - We disclose a Ni-catalyzed regioselective dialkylation reaction of alkenylarenes with α-halocarbonyls and alkylzinc reagents. The reaction produces γ-arylated alkanecarbonyl compounds with the generation of two new C(sp3)−C(sp3) bonds at the vicinal carbons of alkenes. This reaction is effective for the use of primary, secondary and tertiary α-halocarboxylic esters, amides and ketones in conjunction with primary and secondary alkylzinc reagents as the sources of two C(sp3) carbons for the dialkylation of terminal and cyclic internal alkenes.

AB - We disclose a Ni-catalyzed regioselective dialkylation reaction of alkenylarenes with α-halocarbonyls and alkylzinc reagents. The reaction produces γ-arylated alkanecarbonyl compounds with the generation of two new C(sp3)−C(sp3) bonds at the vicinal carbons of alkenes. This reaction is effective for the use of primary, secondary and tertiary α-halocarboxylic esters, amides and ketones in conjunction with primary and secondary alkylzinc reagents as the sources of two C(sp3) carbons for the dialkylation of terminal and cyclic internal alkenes.

UR - https://www.scopus.com/pages/publications/85163607957

UR - https://www.scopus.com/pages/publications/85163607957#tab=citedBy

U2 - 10.1002/anie.202305522

DO - 10.1002/anie.202305522

M3 - Article

C2 - 37316459

AN - SCOPUS:85163607957

SN - 1433-7851

VL - 62

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 32

M1 - e202305522

ER -

Nickel-Catalyzed Regioselective Intermolecular Dialkylation of Alkenylarenes: Generation of Two Vicinal C(sp³)−C(sp³) Bonds Across Alkenes**

Abstract

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