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Co-Catalyzed Cross-Coupling of Alkyl Halides with Tertiary Alkyl Grignard Reagents Using a 1,3-Butadiene Additive

Takanori Iwasaki, Hiroaki Takagawa, Surya P. Singh, Hitoshi Kuniyasu and Nobuaki Kambe*

*Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Suita, Osaka 565-0871, Japan, Email: kambechem.eng.osaka-u.ac.jp

T. Iwasaki, H. Takagawa, S. P. Singh, H. Kuniyasu, N. Kambe, J. Am. Chem. Soc., 2013, 135, 9604-9607.

DOI: 10.1021/ja404285b (free Supporting Information)


Abstract

A cobalt-catalyzed cross-coupling of alkyl (pseudo)halides with alkyl Grignard reagents proceeds via an ionic mechanism in the presence of 1,3-butadiene as a ligand precursor and LiI in high yields and high selectivities. Sterically congested quaternary carbon centers could be constructed by using tertiary alkyl Grignard reagents. This reaction is compatible with various functional groups.


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Key Words

Cross-Coupling


ID: J48-Y2013