Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000131.xml
Synfacts 2011(8): 0885-0885
DOI: 10.1055/s-0030-1260728
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 KunzZ. 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
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)
Key words
nickel - Suzuki coupling - alkyl-alkyl coupling
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.