Bis-silylation of internal alkynes enabled by Ni(0) catalysis

Yun Zhang, Xi-Chao Wang, Cheng-Wei Ju and Dongbing Zhao ()
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Yun Zhang: Nankai University
Xi-Chao Wang: Nankai University
Cheng-Wei Ju: Nankai University
Dongbing Zhao: Nankai University

Nature Communications, 2021, vol. 12, issue 1, 1-10

Abstract: Abstract 1,2-Bis-silyl alkenes have exciting synthetic potential for programmable sequential synthesis via manipulation of the two vicinal silyl groups. Transition metal-catalyzed bis-silylation of alkynes with disilanes is the most straightforward strategy to access such useful building blocks. However, this process has some limitations: (1) symmetric disilanes are frequently employed in most of the reactions to assemble two identical silyl groups, which makes chemoselective differentiation for stepwise downstream transformations difficult; (2) the main catalysts are low-valent platinum group transition metal complexes, which are expensive; and (3) internal alkynes remain challenging substrates with low inherent reactivity. Thus, the development of abundant metal-catalyzed bis-silylation of internal alkynes with unsymmetrical disilanes is of significance. Herein, we solve most of the aforementioned limitations in bis-silylation of unsaturated bonds by developing a strongly coordinating disilane reagent and a Ni(0) catalytic system. Importantly, we sufficiently realize the stepwise recognition of the two silyl groups, making this synthetic protocol of wide potential utility.

Date: 2021
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DOI: 10.1038/s41467-020-20392-w

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