Development of novel syntheses of organophosphorus compounds: from a simple P-C bond formation to phosphacycles

Abstract

Organophosphorus compounds play several essential roles in organic chemistry, such as valuable ligands in transition metal catalysis and functional materials. We have developed versatile organophosphine syntheses via Pd-catalyzed P-C cross-coupling reactions in the course of our study using silylphosphines. Up to three aryl groups can be selectively incorporated into the same phosphorus atom in a stepwise manner. In addition, we found the formation of phosphorus-ylide containing phosphacycles, λ⁵-phosphinines, during the extension of silylphosphine chemistry.

Graphical Abstract

Keywords:

• Organophosphorus compounds
• silylphosphine
• P-C cross-coupling
• phosphacycle
• phosphinine

Acknowledgments

M.H also thanks Division of Applied Protein Research (APR), the Advanced Research Support Center (ADRES), Ehime University for the measurements of NMR spectra.

Disclosure statement

No potential conflict of interest was reported by the author.

Additional information

Funding

M.H. gratefully acknowledges funding by JSPS KAKENHI Grant Number JP15K05430, JP15H00754 and JP18H02022, Grant-in Aid for Scientific Research on Innovative Areas "New Polymeric Materials Based on Element-Blocks (No. 2401)".