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. 2014 Jul 8;70(27-28):4250-4256.
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

Jesse R McAtee  1 , Sara E S Martin  1 , Andrew P Cinderella  1 , William B Reid  1 , Keywan A Johnson  1 , Donald A Watson  1
Affiliations

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

Jesse R McAtee et al. Tetrahedron. .

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.

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Figures

Figure 1
Figure 1
Proposed Mechanism for Silyl-Heck Reaction.
Figure 2
Figure 2
Major byproduct from silyl-Heck reactions of larger silyl triflates.
See this image and copyright information in PMC

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