Highly Regio- and Stereoselective Ni-Catalyzed Hydrocyanation of 1,3-Enynes

Feilong Sun; Jie Ni; Gui-Juan Cheng; Xianjie Fang

doi:10.1002/chem.202000651

Highly Regio- and Stereoselective Ni-Catalyzed Hydrocyanation of 1,3-Enynes

Chemistry. 2020 May 12;26(27):5956-5960. doi: 10.1002/chem.202000651. Epub 2020 Apr 28.

Authors

Feilong Sun¹, Jie Ni², Gui-Juan Cheng², Xianjie Fang¹

Affiliations

¹ Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Frontiers Science Center for Transformative Molecules, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai, 200240, P. R. China.
² Warshel Institute for Computational Biology, School of, Life and Health Sciences, The Chinese University of, Hong Kong (Shenzhen), Shenzhen, 518172, P. R. China.

PMID: 32237171
DOI: 10.1002/chem.202000651

Abstract

A highly regio- and stereoselective hydrocyanation of 1,3-enynes was implemented by nickel/diphosphine catalysts. A wide range of highly regio- and stereoselective alkenyl nitriles were efficiently prepared. In this transformation, both the tethered alkene and the ligand play key roles in the reactivity and selectivity. The origin of regioselectivity was understood preliminarily by DFT studies.

Keywords: 1,3-enynes; alkene effect; alkenyl nitriles; hydrocyanation; nickel.

Abstract

Grants and funding