Organic Chemistry Portal



Highly Z-Selective Double Bond Transposition in Simple Alkenes and Allylarenes through a Spin-Accelerated Allyl Mechanism

Daniel Kim, Guy Pillon, Daniel J. DiPrimio and Patrick L. Holland*

*Department of Chemistry, Yale University, 225 Prospect Street, New Haven, Connecticut 06520, United States, Email:

D. Kim, G. Pillon, D. J. DiPrimio, P. L. Holland, J. Am. Chem. Soc., 2021, 143, 3070-3074.

DOI: 10.1021/jacs.1c00856

see article for more reactions


A β-dialdiminate-supported, high-spin cobalt(I) complex can convert terminal alkenes, including allylbenzenes, to Z-2-alkenes with unprecedentedly high regioselectivity and stereoselectivity. Deuterium labeling studies indicate that the catalyst operates through a π-allyl mechanism.

see article for more examples

Key Words


ID: J48-Y2021