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Nickel-Catalyzed Double Bond Transposition under Kinetic Control

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

Abstract

Taming the reactivity of nickel catalysts is a never-ending inspiration to discover new complexes, ligands, and reaction protocols. Here, we report that a simple combination of Ni(COD)2 and Lewis acids allows activation of allylic CH bonds. Their synergism eases oxidative addition and 1,3-hydrogen atom relocation to yield unprecedented double bond monotransposition. Unique features of this work include polar inner-sphere mechanism, kinetically favored double bond transposition, ligand-controlled stereoselective E or Z isomer distribution, mechanistic insights by control experiments and NMR monitoring.

Keywords

Olefin transposition
Nickel
Isomerization
NMR monitoring

Supplementary materials

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Version History

Nov 25, 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-w9n02
D O I: 10.26434/chemrxiv-2022-w9n02 [opens in a new tab]

Funding

The São Paulo Research Foundation - FAPESP
2018/01669-5
The São Paulo Research Foundation - FAPESP
2019/00080-0
Serrapilheira Institute
Serra-1709-22464
São Paulo Research Foundation
2014/25770-6

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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