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. 2017 Jul 7;19(13):3446-3449.
doi: 10.1021/acs.orglett.7b01421. Epub 2017 Jun 15.

Highly Diastereoselective α-Arylation of Cyclic Nitriles

Michael E Dalziel  1 , Penghao Chen  1 , Diane E Carrera  1 , Haiming Zhang  1 , Francis Gosselin  1
Affiliations

Highly Diastereoselective α-Arylation of Cyclic Nitriles

Michael E Dalziel et al. Org Lett. .

Abstract

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.

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