Unusual nucleophilic reactivity of a dithiolene-based N-heterocyclic silane

Phuong M Tran; Yuzhong Wang; Mitchell E Lahm; Pingrong Wei; Henry F Schaefer 3rd; Gregory H Robinson

doi:10.1039/d3dt03843b

Unusual nucleophilic reactivity of a dithiolene-based N-heterocyclic silane

Dalton Trans. 2024 Apr 2;53(14):6178-6183. doi: 10.1039/d3dt03843b.

Authors

Phuong M Tran¹, Yuzhong Wang¹, Mitchell E Lahm¹, Pingrong Wei¹, Henry F Schaefer 3rd¹, Gregory H Robinson¹

Affiliation

¹ Department of Chemistry, The University of Georgia, Athens, Georgia 30602-2556, USA. robinson@uga.edu.

PMID: 38506299
DOI: 10.1039/d3dt03843b

Abstract

While the dithiolene-based N-heterocyclic silane (4) reacts with two equivalents of BX₃ (X = Br, I) to give zwitterionic Lewis adducts 5 and 8, respectively, the parallel reaction of 4 with BCl₃ results in 10, a dithiolene-substituted N-heterocyclic silane, via the Si-S bond cleavage. Unlike 5, the labile 8 may be readily converted to 9via BI₃-mediated cleavage of the Si-N bond. The formation of 5 and 8 confirms that 4 uniquely possesses dual nucleophilic sites: (a) the terminal sulphur atom of the dithiolene moiety; and (b) the backbone carbon of the N-heterocyclic silane unit.