Ni-Catalyzed Arylbenzylation of Alkenylarenes: Kinetic Studies Reveal Autocatalysis by ZnX2**

Roshan K. Dhungana; Rishi R. Sapkota; Laura M. Wickham; Doleshwar Niroula; Bijay Shrestha; Ramesh Giri

doi:10.1002/anie.202110459

Ni-Catalyzed Arylbenzylation of Alkenylarenes: Kinetic Studies Reveal Autocatalysis by ZnX₂**

Roshan K. Dhungana, Rishi R. Sapkota, Laura M. Wickham, Doleshwar Niroula, Bijay Shrestha, Ramesh Giri

Chemistry

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

15 Scopus citations

Abstract

We report a Ni-catalyzed regioselective arylbenzylation of alkenylarenes with benzyl halides and arylzinc reagents. The reaction furnishes differently substituted 1,1,3-triarylpropyl structures that are reminiscent of the cores of oligoresveratrol natural products. The reaction is also compatible for the coupling of internal alkenes, secondary benzyl halides and variously substituted arylzinc reagents. Kinetic studies reveal that the reaction proceeds with a rate-limiting single-electron-transfer process and is autocatalyzed by in-situ-generated ZnX₂. The reaction rate is amplified by a factor of three through autocatalysis upon addition of ZnX₂.

Original language	English (US)
Pages (from-to)	22977-22982
Number of pages	6
Journal	Angewandte Chemie - International Edition
Volume	60
Issue number	42
DOIs	https://doi.org/10.1002/anie.202110459
State	Published - Oct 11 2021

All Science Journal Classification (ASJC) codes

Catalysis
Chemistry(all)

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@article{5cba4268cb454d6a9b141dc56b018ae7,

title = "Ni-Catalyzed Arylbenzylation of Alkenylarenes: Kinetic Studies Reveal Autocatalysis by ZnX2**",

abstract = "We report a Ni-catalyzed regioselective arylbenzylation of alkenylarenes with benzyl halides and arylzinc reagents. The reaction furnishes differently substituted 1,1,3-triarylpropyl structures that are reminiscent of the cores of oligoresveratrol natural products. The reaction is also compatible for the coupling of internal alkenes, secondary benzyl halides and variously substituted arylzinc reagents. Kinetic studies reveal that the reaction proceeds with a rate-limiting single-electron-transfer process and is autocatalyzed by in-situ-generated ZnX2. The reaction rate is amplified by a factor of three through autocatalysis upon addition of ZnX2.",

author = "Dhungana, {Roshan K.} and Sapkota, {Rishi R.} and Wickham, {Laura M.} and Doleshwar Niroula and Bijay Shrestha and Ramesh Giri",

note = "Funding Information: We gratefully acknowledge the NIH NIGMS (R35GM133438) and The Pennsylvania State University for support of this work, and the PSU NMR facility for NMR support. We thank Mr. Lucas J. Chesley for help with isolation of the product . We thank Mr. Patrick Corrigan in Dr. Silakov's group for help with collecting IR data. 17 Publisher Copyright: {\textcopyright} 2021 Wiley-VCH GmbH",

year = "2021",

month = oct,

day = "11",

doi = "10.1002/anie.202110459",

language = "English (US)",

volume = "60",

pages = "22977--22982",

journal = "Angewandte Chemie - International Edition",

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TY - JOUR

T1 - Ni-Catalyzed Arylbenzylation of Alkenylarenes

T2 - Kinetic Studies Reveal Autocatalysis by ZnX2**

AU - Dhungana, Roshan K.

AU - Sapkota, Rishi R.

AU - Wickham, Laura M.

AU - Niroula, Doleshwar

AU - Shrestha, Bijay

AU - Giri, Ramesh

N1 - Funding Information: We gratefully acknowledge the NIH NIGMS (R35GM133438) and The Pennsylvania State University for support of this work, and the PSU NMR facility for NMR support. We thank Mr. Lucas J. Chesley for help with isolation of the product . We thank Mr. Patrick Corrigan in Dr. Silakov's group for help with collecting IR data. 17 Publisher Copyright: © 2021 Wiley-VCH GmbH

PY - 2021/10/11

Y1 - 2021/10/11

N2 - We report a Ni-catalyzed regioselective arylbenzylation of alkenylarenes with benzyl halides and arylzinc reagents. The reaction furnishes differently substituted 1,1,3-triarylpropyl structures that are reminiscent of the cores of oligoresveratrol natural products. The reaction is also compatible for the coupling of internal alkenes, secondary benzyl halides and variously substituted arylzinc reagents. Kinetic studies reveal that the reaction proceeds with a rate-limiting single-electron-transfer process and is autocatalyzed by in-situ-generated ZnX2. The reaction rate is amplified by a factor of three through autocatalysis upon addition of ZnX2.

AB - We report a Ni-catalyzed regioselective arylbenzylation of alkenylarenes with benzyl halides and arylzinc reagents. The reaction furnishes differently substituted 1,1,3-triarylpropyl structures that are reminiscent of the cores of oligoresveratrol natural products. The reaction is also compatible for the coupling of internal alkenes, secondary benzyl halides and variously substituted arylzinc reagents. Kinetic studies reveal that the reaction proceeds with a rate-limiting single-electron-transfer process and is autocatalyzed by in-situ-generated ZnX2. The reaction rate is amplified by a factor of three through autocatalysis upon addition of ZnX2.

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U2 - 10.1002/anie.202110459

DO - 10.1002/anie.202110459

M3 - Article

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AN - SCOPUS:85114875975

SN - 1433-7851

VL - 60

SP - 22977

EP - 22982

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 42

ER -

Ni-Catalyzed Arylbenzylation of Alkenylarenes: Kinetic Studies Reveal Autocatalysis by ZnX₂**

Abstract

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