Nickel-catalyzed arylative substitution of homoallylic alcohols
Date
2022-08-12
Authors
Major Professor
Advisor
Committee Member
Journal Title
Journal ISSN
Volume Title
Publisher
The Royal Society of Chemistry
Abstract
Direct coupling of unactivated alcohols remains a challenge in synthetic chemistry. Current approaches to cross-coupling of alcohol-derived electrophiles often involve activated alcohols such as tosylates or carbonates. We report the direct arylative substitution of homoallylic alcohols catalyzed by a nickel-bisphosphine complex as a facile method to generate allylic arenes. These reactions proceed via formation of an allylic alcohol intermediate. Subsequent allylic substitution with arylboroxine nucleophiles enables the formation of a variety of allylic arenes. The presence of p-methoxyphenylboronic acid is crucial to activate the allylic alcohol to achieve high product yields.
Series Number
Journal Issue
Is Version Of
Versions
Series
Academic or Administrative Unit
Type
article
Comments
This article is published as Tran, Hai N., Chau M. Nguyen, Mason T. Koeritz, Dustin D. Youmans, and Levi M. Stanley. "Nickel-catalyzed arylative substitution of homoallylic alcohols." Chemical Science 13, no. 39 (2022): 11607-11613.
DOI: 10.1039/D2SC01716D.
Copyright 2022 The Author(s).
Posted with permission.