Organic Letters
Organic Letters
5 years ago

Highly Diastereoselective α-Arylation of Cyclic Nitriles

Highly Diastereoselective α-Arylation of Cyclic Nitriles
Francis Gosselin, Diane E. Carrera, Haiming Zhang, Penghao Chen, Michael E. Dalziel
A highly diastereoselective α-arylation of cyclic nitriles has been developed via a Negishi cross-coupling of commercially available aryl, heteroaryl, and alkenyl halides with cyclobutyl nitriles in the presence of tetramethylpiperidinylzinc chloride lithium chloride (TMPZnCl•LiCl) and catalytic XPhos-Pd-G2. A variety of electronically diverse electrophiles were well tolerated, and this chemistry was further advanced with application of both cyclopropyl and cyclopentyl nitriles.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01421

DOI: 10.1021/acs.orglett.7b01421

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