The first example of nickel-catalyzed silyl-Heck reactions: direct activation of silyl triflates without iodide additives

• DOI: 10.1016/j.tet.2014.03.021
• Publication Date: 2014-03-18T07:46:30Z
• Authors: Jesse R. McAtee; Sara E.S. Martin; Andrew P. Cinderella; William B. Reid; Keywan A. Johnson; Donald A. Watson
• Keywords: 01 natural sciences; 0104 chemical sciences

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.