Enantioposition-selective arylation of biaryl ditriflates by palladium-catalyzed asymmetric Grignard cross-coupling

✍ Scribed by Takashi Kamikawa; Tamio Hayashi

• Book ID: 104209074
• Publisher: Elsevier Science
• Year: 1999
• Tongue: French
• Weight: 869 KB
• Volume: 55
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(98)01154-5

✦ Synopsis

Asymmetric cross-coupling of achiral biaryl ditriflates with aryl Grignard reagents in the presence of 1 equiv of lithium bromide and 5 tool % of palladium complex PdC12[(S)-alaphos], where alaphos stands for (2dimethylamino)propyldiphenylphosphine, gave axially chiral monophenylation products with high enantioposition-selectivity. The remaining triflate group in the monophenylation products was substituted with carboxyl and diphenylphosphino groups through palladium-catalyzed carbonylation and diphenylphosphinylation, respectively.