Organophosphine syntheses via activation of the phosphorus-silicon bond of silylphosphines.
This paper describes the recent advances in the syntheses of organophosphines by forming several types of phosphorus-carbon bonds via activation of the phosphorus-silicon bond of silylphosphines. In this account, the activation methods are classified into three types: nucleophile-induced activations, reactions with Lewis acid-activated electrophiles, and transition metal catalyzed reactions. Nucleophile-induced activations of silylphosphines, especially by a fluoride, generated a reactive phosphide equivalent for selective formation of a P-C bond. Silylphosphines also reacted selectively with Lewis acid-activated electrophiles. The Lewis acid mediated/catalyzed additions and substitutions, to form sp3-carbon-phosphorus bonds including an asymmetric reaction, are described. Several important types of transition metal catalyzed reactions of silylphosphines are also mentioned in this account. Selective formation of a P-C bond is achieved through these activations to produce a variety of functional organophosphines including optically active ones.
Hayashi
Minoru
M
Department of Materials Science and Biotechnology, Graduate School of Science and Engineering, Ehime University, 3 Bunkyo-cho, Matsuyama 790-8577, Japan. hayashi@eng.ehime-u.ac.jp
D002384:Catalysis; D010720:Phosphines / Q000138:chemical synthesis*; D010758:Phosphorus / Q000737:chemistry; D012825:Silicon / Q000737:chemistry
D010720:Phosphines; D010758:Phosphorus; C044646:phosphine; D012825:Silicon