Synfacts 2007(1): 0081-0081  
DOI: 10.1055/s-2006-955708
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Ru-Catalyzed Regiospecific Borylation of Methyl C-H Bonds

Contributor(s): Paul Knochel, Andrei Gavryushin
J. M. Murphy, J. D. Lawrence, K. Kawamura, C. Incarvito, J. F. Hartwig*
Yale University, New Haven and University of Illinois, Urbana, USA
Further Information

Publication History

Publication Date:
15 December 2006 (online)

Significance

Alkylboronic derivatives are recently gaining interest as synthetic intermediates, due to the raising amount of newly discovered transformations involving these versatile organometallics. Direct catalytic C-H activation is a new synthetic approach which is of great interest and offers new ways of functionalization of organic substrates. This is the first report of the use of relatively inexpensive ruthenium catalysis for the borylation of simple alkanes. The reaction is highly selective for Me groups and requires 2-5 mol% of Ru species as catalyst. β-Amino- and -alkoxyboronic derivatives, unavailable by conventional organometallic methods, can be obtained from the corresponding N- and O-alkyl species using this elegant approach.