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Published June 1, 2011 | Accepted Version + Supplemental Material
Journal Article Open

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

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.

Additional Information

© 2011 American Chemical Society. Received: April 18, 2011. Published: May 10, 2011. This study is dedicated to the memory of Prof. David Y. Gin. Support has been provided by the National Institutes of Health (National Institute of General Medical Sciences, Grant R01-GM62871), Eli Lilly (fellowship to Z.L.), and the Martin Family Society of Fellows for Sustainability (fellowship to Z.L.).

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Accepted Version - nihms295619.pdf

Supplemental Material - ja203560q_si_001.pdf

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August 22, 2023
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