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Nickel-catalyzed 1,4-rearrangement of an aryl Group in aryl N-benzylimidates via C–O and C–H bond cleavage

26 April 2022, Version 1
Working Paper
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

We report herein that nickel-catalyzed reaction of aryl imidates bearing an N-benzyl group results in 1,4-migration of an O-aryl group via the cleavage of C–O and C–H bonds. This protocol allows for the benzylic C–H bond arylation of benzylamine building blocks using phenols as an aryl source to form elaborate diarylmethylamine derivatives.

Keywords

nickel catalyst
C-O activation
C-H activation

Supplementary materials

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Detailed experimental procedures and spectroscopic data for new compounds.
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Now Published

Nickel-catalyzed 1,4-aryl rearrangement of aryl N-benzylimidates via C–O and C–H bond cleavage [opens in a new tab]
Satoshi Ogawa, Mamoru Tobisu journal article
Chemical Communications , Volume 58, Issue 57
Online publication date: 2022

Version History

Apr 26, 2022 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-2022-rf4s5
D O I: 10.26434/chemrxiv-2022-rf4s5 [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) have declared ethics committee/IRB approval is not relevant to this content

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