Issue 72, 2024

Stereodivergent sila-germylenation vs. sila-stannylenation of an internal alkyne

Abstract

We report on the insertion of electron deficient alkyne, dimethyl acetylene dicarboxylate (DMAD), into the E–Si bond of hypersilyl tetrylenes, PhC(NtBu)2ESi(SiMe3)3 (E = Ge and Sn), at room temperature. Uniquely, the germylene leads to cis alkenes, while the stannylene gives access to trans alkenes, and the insight into divergent stereoselectivity has been obtained by DFT studies.

Graphical abstract: Stereodivergent sila-germylenation vs. sila-stannylenation of an internal alkyne

Supplementary files

Article information

Article type
Communication
Submitted
30 4 2024
Accepted
13 8 2024
First published
14 8 2024

Chem. Commun., 2024,60, 9837-9840

Stereodivergent sila-germylenation vs. sila-stannylenation of an internal alkyne

V. S. Ajithkumar, P. B. Ghanwat, S. Saha, S. K. Pati and S. S. Sen, Chem. Commun., 2024, 60, 9837 DOI: 10.1039/D4CC02101K

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