nBuLi-Mediated Hydrophosphination: A Simple Route to Valuable Organophosphorus Compounds

✍ Scribed by Arnaud Perrier; Virginie Comte; Claude Moïse; Philippe Richard; Pierre Le Gendre

• Publisher: John Wiley and Sons
• Year: 2010
• Tongue: English
• Weight: 493 KB
• Volume: 2010
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/ejoc.200901407

✦ Synopsis

Abstract

A straightforward synthesis of homoallyl‐ and allylphosphanes has been developed using __n__BuLi‐mediated hydrophosphination of conjugated dienes. In all the cases the phosphorus atom of the reacting phosphane attacked thesterically less demanding side of the diene exclusively. In addition, high regioselectivities towards 1,2‐ or 1,4‐addition products were observed depending on the nature of the dienes. This hydrophosphination reaction was extended to a variety of substrates such as styrene derivatives, alkynes and 1,3,5‐cycloheptatriene. The structures of three hydrophosphination products were confirmed by X‐ray diffractionstudies.