Issue 25, 2021

An air-stable, Zn2+-based catalyst for hydrosilylation of alkenes and alkynes

Abstract

Hydrosilylation of C[double bond, length as m-dash]C double and C[triple bond, length as m-dash]C triple bonds is one of the most widely used processes in organosilicon chemistry, mostly catalyzed by Pt-based complexes. We report here the synthesis of an air-stable dicationic Zn2+-based complex in a hemilabile tris(2-methyl-6-pyridylmethyl) phosphine (TmPPh) ligand, 12+[B(C6F5)4]2. When heated, 12+[B(C6F5)4]2 activates Si–H bonds reversibly via ligand/metal cooperation between Lewis acidic Zn2+ and Lewis basic N centers in a frustrated Lewis pair (FLP) type fashion. Consequently, 12+[B(C6F5)4]2 was found to be an effective catalyst for hydrosilylation reactions of C[double bond, length as m-dash]C double and C[triple bond, length as m-dash]C triple bonds. Remarkably, these hydrosilylation reactions can be loaded under aerobic conditions, as well as, in some cases, work under neat conditions. The mechanism of the activation of the Si–H bond and the hydrosilylation reaction is proposed based on experiments and density functional theory (DFT) calculations.

Graphical abstract: An air-stable, Zn2+-based catalyst for hydrosilylation of alkenes and alkynes

Supplementary files

Article information

Article type
Paper
Submitted
22 Dzi 2021
Accepted
25 Mud 2021
First published
25 Mud 2021

Org. Biomol. Chem., 2021,19, 5544-5550

An air-stable, Zn2+-based catalyst for hydrosilylation of alkenes and alkynes

K. Groutchik, K. Jaiswal and R. Dobrovetsky, Org. Biomol. Chem., 2021, 19, 5544 DOI: 10.1039/D1OB00782C

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