The coupling reaction of copper(I) methyltrialkylborates with aroyl chlorides. A convenient synthesis of alkyl aryl ketones from organoboranes

✍ Scribed by Norio Miyaura; Norio Sasaki; Mitsuomi Itoh; Akira Suzuki

• Publisher: Elsevier Science
• Year: 1977
• Tongue: French
• Weight: 129 KB
• Volume: 18
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)92580-8

✦ Synopsis

Recently, we have reported that copper(I) methyltrialkylborates readily undergo addition reactions to acrylonitrile, ethyl acrylate, and 1-acyl-Z-vinylcyclopropane.' These reagents also react with relatively active halides such as benzyl,2 allyl, and propargyl halides. 3 Inan attempt to develop the reaction of such borates, we examined the possibility of a coupling reaction with aroyl chlorides. To the solution of copper(I) methyltripropylborate obtained from lithium methyltripropylborate and copper(I) halides (eq. 1), benzoyl chloride was added at O°C and stirred at room