Stereoconvergent Amine-Directed Alkyl–Alkyl Suzuki Reactions of Unactivated Secondary Alkyl Chlorides

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–enantiose...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2011-06, Vol.133 (21), p.8154-8157
Main Authors: Lu, Zhe, Wilsily, Ashraf, Fu, Gregory C
Format: Article
Language:English
Subjects:
Amines - chemistry
Catalysis
Chlorides - chemistry
Molecular Structure
Nickel
Stereoisomerism
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Summary: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.
ISSN:0002-7863
1520-5126
1520-5126
DOI:10.1021/ja203560q