Iowa State University Research Foundation, Inc.

Jerzy W Wiench

Vitalij K Pecharsky

Viktor Balema

Marek Pruski

The present invention provides a method of preparing a phosphonium salt of the formula [RRRP&#x2014;CRRR]X, comprising ball-milling a phosphine of the formula RRRP with a compound of the formula XCRRR; a method of preparing a phosphorus ylide of the formula RRRP&#x2550;CRR, comprising ball-milling a phosphonium salt of the formula [RRRP&#x2014;HCRR]X in the presence of a base; and a method of preparing an olefin of the formula RRC&#x2550;CRH or RRC&#x2550;CRR, comprising ball-milling a phosphorus ylide of the formula RRRP&#x2550;CRRwith a compound of the formula RC(O)H or RC(O)R. The inventive method produces phosphonium salts and phosphorus ylides by mechanical processing solid reagents under solvent-free conditions. The advantages of the present invention over conventional solution methods, include: (1) extremely high selectivity; (2) high yields; (3) low processing temperatures; (4) simple and scalable reactions using commercially available equipment; and (5) the complete elimination of solvents from the reaction.

Solvent-free mechanochemical preparation of phosphonium salts, phosphorus ylides, and olefins

The present invention provides a method of preparing a phosphonium salt of the formula &lsqb;R R R P&mdash;CR R R &rsqb;X, comprising ball-milling a phosphine of the formula R R R P with a compound of the formula XCR R R ; a method of preparing a phosphorus ylide of the formula R R R P&boxH;CR R , comprising ball-milling a phosphonium salt of the formula &lsqb;R R R P&mdash;HCR R &rsqb;X in the presence of a base; and a method of preparing an olefin of the formula R R C&boxH;CR H or R R C&boxH;CR R , comprising ball-milling a phosphorus ylide of the formula R R R P&boxH;CR R with a compound of the formula R C(O)H or R C(O)R . The inventive method produces phosphonium salts and phosphorus ylides by mechanical processing solid reagents under solvent-free conditions. The advantages of the present invention over conventional solution methods, include: (1) extremely high selectivity; (2) high yields; (3) low processing temperatures; (4) simple and scalable reactions using commercially available equipment; and (5) the complete elimination of solvents from the reaction.

Growing community of inventors

Ames, IA, United States of America

Jerzy W Wiench