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:
kambe
chem.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
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.
see article for more examples
J. Terao, Y. Naitoh, H. Kuniyasu, N. Kambe, Chem. Lett., 2003, 890-891.
Key Words
ID: J48-Y2013
