Mechanistic Studies of Nickel-Catalyzed Hydroarylation of Styrenes

The mechanism of nickel-catalyzed hydroarylation of styrenes has been explored with density functional theory. Instead of the stepwise pathway via a Ni­(II)–H species, computational results unveil that the concerted RO–H oxidative addition/olefin insertion takes place kinetically favorable to genera...

Full description

Saved in:
Bibliographic Details
Published inOrganic letters Vol. 22; no. 22; pp. 8998 - 9003
Main Authors Cheng, Qi, Dang, Yanfeng
Format Journal Article
LanguageEnglish
Published American Chemical Society 20.11.2020
Online AccessGet full text

Cover

More Information
Summary:The mechanism of nickel-catalyzed hydroarylation of styrenes has been explored with density functional theory. Instead of the stepwise pathway via a Ni­(II)–H species, computational results unveil that the concerted RO–H oxidative addition/olefin insertion takes place kinetically favorable to generate the alkylnickel­(II) species, which further undergoes transmetalation and reductive elimination to yield the hydroarylated product. The origins of regio- and stereoselectivity were revealed via analyzing the electronic and steric effects of the key transition states.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c03395