Stannylene cyanide and its use as a cyanosilylation catalyst

Vivek Kumar Singh; Prakash Chandra Joshi; Hemant Kumar; Rahul Kumar Siwatch; Chandan Kumar Jha; Selvarajan Nagendran

doi:10.1039/d2dt02721f

Stannylene cyanide and its use as a cyanosilylation catalyst

Dalton Trans. 2022 Nov 15;51(44):16906-16914. doi: 10.1039/d2dt02721f.

Authors

Vivek Kumar Singh¹, Prakash Chandra Joshi¹, Hemant Kumar¹, Rahul Kumar Siwatch¹, Chandan Kumar Jha¹, Selvarajan Nagendran¹

Affiliation

¹ Department of Chemistry, Indian Institute of Technology Delhi, Hauz Khas, New Delhi 110016, India. sisn@chemistry.iitd.ac.in.

PMID: 36301048
DOI: 10.1039/d2dt02721f

Abstract

Two routes can offer the first stannylene cyanide [(L)SnCN] (5); the substitution reaction of either stannylene amide [(i-Bu)₂ATISnN(SiMe₃)₂] (3) or stannylene pyrrolide [(i-Bu)₂ATISn(NC₄H₄)] (4) using an excess of trimethylsilyl cyanide (L = aminotroponiminate (ATI)). Using 0.1-2.0 mol% of compound 5, catalytic cyanosilylation of a variety of aliphatic and aromatic aldehydes was achieved at rt-50 °C in 0.33-2.0 h. The mechanism of this catalytic reaction is authenticated by the isolation of a structurally characterized intermediate.