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Nickel-Catalyzed Coupling Reactions of Alkyl Electrophiles, Including Unactivated Tertiary Halides, To Generate Carbon-Boron Bonds

Alexander S. Dudnik and Gregory C. Fu*

*Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, United States, Email: gcfmit.edu

A. S. Dudnik, G. C. Fu, J. Am. Chem. Soc., 2012, 134, 10693-10697.

DOI: 10.1021/ja304068t (free Supporting Information)


Abstract

A catalyst formed in situ from NiBr2 • diglyme and a pybox ligand accomplishes Miyaura-type borylations of unactivated tertiary, secondary, and primary alkyl halides with diboron reagents to furnish alkylboronates. The method exhibits good functional-group compatibility and is regiospecific.

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Key Words

Alkylboronates, Miyaura Borylation


ID: J48-Y2012-2030