Facile synthesis of aryl(difluoromethyl)phosphonates through CuBr-mediated cross coupling reactions of [(diethoxyphosphinyl)difluoromethyl]zinc bromide with aryl iodides

✍ Scribed by Tsutomu Yokomatsu; Tetsuo Murano; Kenji Suemune; Shiroshi Shibuya

• Book ID: 104207438
• Publisher: Elsevier Science
• Year: 1997
• Tongue: French
• Weight: 566 KB
• Volume: 53
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(96)01063-0

✦ Synopsis

The CuBr-promoted coupling reaction of [(dicthoxyphosphinyI)difluoromcthyI]~inc bromide 6 with aryl iodidcs in either DMF or DMA was cxamincd to give a series of aryl(difluoromcthyl)phosphonales. The coupling reaction was applicable to the sclcclive synthesis ol~a,a-difluoro+iodobcnzylphosphonale 1 le, a useful intcrmcdiale for the preparation of F,Pmp. I-[(Diethylphosphono)difluoromcthyl]naphthalcnc 15 and Ihc rcgioisomer 16 were obrained in high yields from I-and 2Godonaphthalcne, respcctivcly. The phosphonatc 16 was transformed to the free acid 4a, a low molecular-mass inhibitor of protcm phosphalascs.