Solvent-free mechanochemical preparation of phosphonium salts, phosphorus ylides, and olefins
US6730812B2 · kind B2 · utility
Assignee
Inventors
Key dates
| Filing date | Feb 5, 2003 |
| Grant date | May 4, 2004 |
| Priority date | — |
| Expiry date | Feb 5, 2023 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07F9/54
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
The present invention provides a method of preparing a phosphonium salt of the formula [R1R2R3P—CR4R5R6]X, comprising ball-milling a phosphine of the formula R1R2R3P with a compound of the formula XCR4R5R6; a method of preparing a phosphorus ylide of the formula R1R2R3P═CR4R5, comprising ball-milling a phosphonium salt of the formula [R1R2R3P—HCR4R5]X in the presence of a base; and a method of preparing an olefin of the formula R4R5C═CR7H or R4R5C═CR7R8, comprising ball-milling a phosphorus ylide of the formula R1R2R3P═CR4R5 with a compound of the formula R7C(O)H or R7C(O)R8. 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.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.