Synfacts 2011(8): 0885-0885  
DOI: 10.1055/s-0030-1260728
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Amine-Directed Alkyl-Alkyl Suzuki Reactions

Contributor(s):Paul Knochel, Thomas Kunz
Z. Lu, A. Wilsily, G. C. Fu*
Massachusetts Institute of Technology, Cambridge, USA
Stereoconvergent Amine-Directed Alkyl-Alkyl Suzuki Reactions of Unactivated Secondary Alkyl Chlorides
J. Am. Chem. Soc.  2011,  133:  8154-8157  
Further Information

Publication History

Publication Date:
20 July 2011 (online)


Significance

This work reports the development of a stereoconvergent aryl amine directed alkyl-alkyl Suzuki coupling. In this protocol, unactivated secondary alkyl chlorides serve as substrates and the desired products are generally obtained with good enantioselectivity using a C 2-symmetric 1,2-diamine ligand.

Comment

Structure-enantioselectivity studies indicated that the aryl amine is the primary coordination site to the catalyst. Consistently, the introduction of an additional methylene unit between the aryl amine moiety and the chloride leads to a product with essentially no enantiomeric excess.