Nickel catalyzed cross-coupling of modified alkyl and alkenyl Grignard reagents with aryl- and heteroaryl nitriles: activation of the CCN bond

✍ Scribed by Joseph A Miller; John W Dankwardt

• Publisher: Elsevier Science
• Year: 2003
• Tongue: French
• Weight: 120 KB
• Volume: 44
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(03)00075-3

✦ Synopsis

The nickel catalyzed cross-coupling of alkyl and alkenyl Grignard reagents with aryl nitrile derivatives affords good yields of the corresponding aryl alkanes or aryl alkenes via activation of the C CN bond. To prevent direct addition of the nucleophile to the nitrile group, the reactivity of the Grignard reagent was modulated by reaction with either LiOt-Bu or PhSLi prior to cross-coupling. The optimum catalyst was determined to be NiCl 2 (PMe 3 ) 2 , which is a convenient air stable commercially available complex.