Metal-free σ-bond metathesis in 1,3,2-diazaphospholene-catalyzed hydroboration of carbonyl compounds

Research output: Journal Publications and Reviews (RGC: 21, 22, 62)21_Publication in refereed journalpeer-review

154 Scopus Citations
View graph of relations



Original languageEnglish
Pages (from-to)190-194
Journal / PublicationAngewandte Chemie - International Edition
Issue number1
Publication statusPublished - 2 Jan 2015
Externally publishedYes


The first metal-free catalytic hydroboration of carbonyl derivatives has been developed in which a catalytic amount of 1,3,2-diazaphospholene effectively promotes a hydroboration reaction of aliphatic and aromatic aldehydes and ketones. The reaction mechanism involves the cleavage of both the P-O bond of the alkoxyphosphine intermediate and the B-H bond of pinacolborane as well as the formation of P-H and B-O bonds. Thus, the reaction proceeds through a non-metal s-bond metathesis. Kinetic and computational studies suggest that the s-bond metathesis occurred in a stepwise but nearly concerted manner.

Research Area(s)

  • Hydroboration, Main-group catalysts, Metal-free catalysis, Phosphanes, σ -bond metathesis