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. 2015 Sep 23;137(37):11876-9.
doi: 10.1021/jacs.5b06740. Epub 2015 Sep 10.

α-Arylation of Saturated Azacycles and N-Methylamines via Palladium(II)-Catalyzed C(sp(3))-H Coupling

Jillian E Spangler  1 , Yoshihisa Kobayashi  2 , Pritha Verma  1 , Dong-Hui Wang  1 , Jin-Quan Yu  1
Affiliations

α-Arylation of Saturated Azacycles and N-Methylamines via Palladium(II)-Catalyzed C(sp(3))-H Coupling

Jillian E Spangler et al. J Am Chem Soc. .

Abstract

Pd(II)-catalyzed α-C(sp(3))-H arylation of pyrrolidines, piperidines, azepanes, and N-methylamines with arylboronic acids has been developed for the first time. This transformation is applicable to wide arrays of pyrrolidines and boronic acids, including heteroaromatic boronic acids. A diastereoselective one-pot heterodiarylation of pyrrolidines has also been achieved.

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Figures

Scheme 1
Scheme 1
Stoichiometric α-Arylation of Pyrrolidine
Scheme 2
Scheme 2
Arylation of Larger Azacycles
Scheme 3
Scheme 3
Deprotection of Thioamide
See this image and copyright information in PMC

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