The First Example of Nickel-Catalyzed Silyl-Heck Reactions: Direct Activation of Silyl Triflates Without Iodide Additives

Jesse R McAtee; Sara E S Martin; Andrew P Cinderella; William B Reid; Keywan A Johnson; Donald A Watson

doi:10.1016/j.tet.2014.03.021

The First Example of Nickel-Catalyzed Silyl-Heck Reactions: Direct Activation of Silyl Triflates Without Iodide Additives

Tetrahedron. 2014 Jul 8;70(27-28):4250-4256. doi: 10.1016/j.tet.2014.03.021.

Authors

Jesse R McAtee¹, Sara E S Martin¹, Andrew P Cinderella¹, William B Reid¹, Keywan A Johnson¹, Donald A Watson¹

Affiliation

¹ Department of Chemistry and Biochemistry, University of Delaware, Newark, DE, 19716.

Abstract

For the first time, nickel-catalyzed silyl-Heck reactions are reported. Using simple phosphine-supported nickel catalysts, direct activation of silyl triflates has been achieved. These results contrast earlier palladium-catalyzed systems, which require iodide additives to activate silyl-triflates. These nickel-based catalysts exhibit good functional group tolerance in the preparation of vinyl silanes, and unlike earlier systems, allows for the incorporation of trialkylsilanes larger than Me₃Si.

Abstract

Grants and funding