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

12 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

Cite this

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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 = "Funding Information: We gratefully acknowledge the NIH NIGMS (R35GM133438) and The Pennsylvania State University (PSU) for support of this work. We thank Dr. Christy George at the PSU NMR facility for help with stereochemistry determination of product . 45 Publisher Copyright: {\textcopyright} 2023 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.",

year = "2023",

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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

N1 - Funding Information: We gratefully acknowledge the NIH NIGMS (R35GM133438) and The Pennsylvania State University (PSU) for support of this work. We thank Dr. Christy George at the PSU NMR facility for help with stereochemistry determination of product . 45 Publisher Copyright: © 2023 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.

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.

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