ACS Catalysis
ACS Catalysis
4 years ago

Copper-Catalyzed Functionalized Tertiary-Alkylative Sonogashira Type Couplings via Copper Acetylide at Room Temperature

Copper-Catalyzed Functionalized Tertiary-Alkylative Sonogashira Type Couplings via Copper Acetylide at Room Temperature
Yu Yamane, Naoki Miwa, Takashi Nishikata
There are several reports on Sonogashira couplings, but most of the reported reactions have employed aryl or alkenyl halides as coupling partners. Therefore, Sonogashira coupling is unsuitable for alkyl loadings, especially tertiary alkyl groups. In this research, we found that a copper catalyst is effective for a reaction between a terminal alkyne and an α-bromocarbonyl compound to form a quaternary carbon having alkynyl group at room temperature. Control experiments revealed that a copper acetylide is a key intermediate.

Publisher URL: http://dx.doi.org/10.1021/acscatal.7b02615

DOI: 10.1021/acscatal.7b02615

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