Nickel-Catalyzed Double Bond Transposition under Kinetic Control

25 November 2022, Version 1
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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