The first nickel-catalyzed alkenylation of unactivated C(sp(3))-H bonds with vinyl iodides is described. The catalytic system comprises an inexpensive and air-stable Ni(acac)2 as the catalyst and BINOL as the ligand, which is highly efficient for the alkenylation of β-methyl C(sp(3))-H bonds of a broad range of aliphatic carboxamides. The resulting olefins can serve as versatile handles for further preparation. Additionally, we also demonstrated the synthesis of functionalized carboxamides bearing α-quaternary carbon centers from simple pivalamide via nickel-catalyzed sequential C(sp(3))-H bond functionalization.

Download full-text PDF

Source
http://dx.doi.org/10.1039/c5cc02254aDOI Listing

Publication Analysis

Top Keywords

csp3-h bonds
12
alkenylation unactivated
8
unactivated csp3-h
8
niii/binol-catalyzed alkenylation
4
csp3-h
4
bonds nickel-catalyzed
4
nickel-catalyzed alkenylation
4
bonds vinyl
4
vinyl iodides
4
iodides described
4

Similar Publications

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!