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Organophotoredox/Ni-Cocatalyzed Allylation of Allenes: Regio-, and Diastereoselective Access to Homoallylic Alcohols

27 December 2021, Version 1
Working Paper
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

A dual organophotoredox/nickel-catalyzed reductive coupling of allenes with aldehydes has been developed for the rapid assembly of anti-homoallylic alcohols with high levels of regioselectivities (>20:1), and diastereoselectivities (up to >20:1) and yields (up to 91%). The allylation was realized through a crucial π-allylnickel intermediate which was obtained via insertion of allenes with a Ni−H intermediate. Moreover, γ,γ-disubstituted homoallylic alcohols with a quaternary stereocenter can also be prepared by this protocol.

Keywords

photoredox
nickel
allylation
homoallylic alcohol
allene

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Version History

Dec 27, 2021 Version 1

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The content is available under CC BY NC ND 4.0 [opens in a new tab]

DOI

10.26434/chemrxiv-2021-kmlk8
D O I: 10.26434/chemrxiv-2021-kmlk8 [opens in a new tab]

Author’s competing interest statement

The author(s) have declared they have no conflict of interest with regard to this content

Ethics

The author(s) declare that they have sought and gained approval from the relevant ethics committee/IRB for this research and its publication.

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