Stereoconvergent Amine-Directed Alkyl–Alkyl Suzuki Reactions of Unactivated Secondary Alkyl Chlorides
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Fu_Stereoconvergent amine.pdf
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Author(s)
Lu, Zhe
Wilsily, Ashraf
Fu, Gregory C.
Date Issued
May 2011
Journal
Journal of the American Chemical Society
Publisher
American Chemical Society (ACS)
Citation
Lu, Zhe, Ashraf Wilsily, and Gregory C. Fu. “Stereoconvergent Amine-Directed Alkyl–Alkyl Suzuki Reactions of Unactivated Secondary Alkyl Chlorides.” Journal of the American Chemical Society 133, no. 21 (June 2011): 8154-8157.
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Author's final manuscript
Abstract
A new family of stereoconvergent cross-couplings of unactivated secondary alkyl electrophiles has been developed, specifically, arylamine-directed alkyl–alkyl Suzuki reactions. This represents the first such investigation to be focused on the use of alkyl chlorides as substrates. Structure–enantioselectivity studies are consistent with the nitrogen, not the aromatic ring, serving as the primary site of coordination of the arylamine to the catalyst. The rate law for this asymmetric cross-coupling is compatible with transmetalation being the turnover-limiting step of the catalytic cycle.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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DOI of Published Version
https://doi.org/10.1021/ja203560q
