Cyclic phosphine oxides and phosphinamides from di-grignard reagents and phosphonic dichlorides: modular access to annulated phospholanes

Authors

Aaron M. Gregson, University of WollongongFollow
Steven M. Wales, University of WollongongFollow
Stephen Bailey, University of WollongongFollow
Anthony C. Willis, Australian National University
Paul A. Keller, University of WollongongFollow

RIS ID

103333

Publication Details

Gregson, A. M., Wales, S. M., Bailey, S. J., Willis, A. C. & Keller, P. A. (2015). Cyclic phosphine oxides and phosphinamides from di-grignard reagents and phosphonic dichlorides: modular access to annulated phospholanes. Journal of Organic Chemistry, 80 (19), 9774-9780.

Abstract

The reaction between 1,4-di-Grignard reagents and phosphonous(III) dichlorides is a classical method for the direct synthesis of phospholanes. Reported here is an extension of this approach to the preparation of value-added, annulated phospholane oxides, achieved through the combination of carbocyclic-fused di-Grignard reagents and readily available phosphonic(V) dichlorides. The procedure is amenable to (benz)annulation at both the 2,3- and 3,4-positions of the phospholane ring, and a variety of aliphatic, cyclic and aryl P-electrophiles are tolerated in reasonable to excellent yields.