Nickel-catalyzed intermolecular coupling of 1,3-dienes and aldehydes via transmetalation of nickelacycles with diisobutylaluminum acetylacetonate

Yoshihiro Sato; Rieko Sawaki; Nozomi Saito; Miwako Mori

doi:10.1021/jo0106086

Nickel-catalyzed intermolecular coupling of 1,3-dienes and aldehydes via transmetalation of nickelacycles with diisobutylaluminum acetylacetonate

J Org Chem. 2002 Feb 8;67(3):656-62. doi: 10.1021/jo0106086.

Authors

Yoshihiro Sato¹, Rieko Sawaki, Nozomi Saito, Miwako Mori

Affiliation

¹ Graduate School of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan.

PMID: 11856003
DOI: 10.1021/jo0106086

Abstract

Intermolecular coupling reactions of 1,3-dienes and aldehydes via transmetalation of nickelacycle intermediate with (i)Bu(2)Al-acac were investigated. In the reactions, a linear adduct or a branched adduct was produced, depending upon the nature of 1,3-dienes and aldehydes, via two nickelacycles that were relatively stable among the four possible nickelacycles because of the equilibrium with pi-allynickel forms.