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Synfacts 2012; 8(10): 1125
DOI: 10.1055/s-0032-1317216
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Cu-Catalyzed Coupling of Secondary Alkyl Electrophiles and Alkyl Grignards

Contributor(s):
Paul Knochel
,
Andreas K. Steib
Yang C.-T, Zhang Z.-Q, Liang J, Liu J.-H, Lu X.-Y, Chen H.-H, Liu L * Tsinghua University, Beijing and University of Science and Technology of China, Hefei, P. R. of China
Copper-Catalyzed Cross-Coupling of Nonactivated Secondary Alkyl Halides and Tosylates with Secondary Alkyl Grignard Reagents.

J. Am. Chem. Soc. 2012;
134: 11124-11127
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Publication History

Publication Date:
19 September 2012 (online)

 
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Key words

copper - inversion - Grignard reagents

Significance

A novel method for the cross-­coupling of nonactivated secondary alkyl halides and pseudo halides with secondary Grignard reagents with a copper catalyst is described. The addition of TMEDA and LiOMe was found to be crucial for the success of the reaction. A broad range of functional groups including esters, amides and aryl ­halides, is tolerated under the reaction conditions.


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Comment

Interestingly, the reaction proceeds according to a classical SN2 mechanism with inversion of configuration. Therefore, easily accessible chiral secondary alcohols can be converted into chiral tosylates and alkylated with a copper-catalyst with either primary or secondary alkyl ­Grignard reagents to furnish the products in high enantiomeric excess.


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