ATI stabilized germylene cation as a cyanosilylation catalyst for aldehydes and ketones

Vivek Kumar Singh; Dharmendra Singh; Hemant Kumar; Prakash Chandra Joshi; Vishal Singh; Pratima Shukla; Tanu Sharma; Gopalan Rajaraman; Selvarajan Nagendran

doi:10.1002/asia.202400138

ATI stabilized germylene cation as a cyanosilylation catalyst for aldehydes and ketones

Chem Asian J. 2024 May 11:e202400138. doi: 10.1002/asia.202400138. Online ahead of print.

Authors

Vivek Kumar Singh¹, Dharmendra Singh², Hemant Kumar², Prakash Chandra Joshi², Vishal Singh², Pratima Shukla², Tanu Sharma³, Gopalan Rajaraman³, Selvarajan Nagendran⁴

Affiliations

¹ Indian Institute of Technology Delhi, Chemistry, 110016, New Delhi, INDIA.
² Indian Institute of Technology Delhi, Chemistry, INDIA.
³ Indian Institute of Technology Bombay, Chemistry, INDIA.
⁴ Indian Institute of Technology Delhi, Department of Chemistry, Hauz Khas, 110 016, New Delhi, INDIA.

PMID: 38733617
DOI: 10.1002/asia.202400138

Abstract

The aminotroponiminate (ATI) ligand stabilized germylene cation [(i-Bu)2ATIGe][B(C6F5)4] (2) is found to be an efficient low-valent main-group catalyst for the cyanosilylation of aldehydes and ketones (ATI = aminotroponiminate). It was synthesized by reacting [(i-Bu)2ATIGeCl] (1) with Na[B(C6F5)4]. The catalytic cyanosilylation of diverse aliphatic and aromatic carbonyl compounds (aldehydes and ketones) using 0.075-0.75 mol% of compound 2 was completed within 5-45 min. The catalytic efficiency seen with aliphatic aldehydes was around 15,800 h-1, making compound 2 a capable low-valent main-group catalyst for the aldehyde and ketone cyanosilylation reactions.

Keywords: Catalysis; Cyanosilylation; Germylene; Germylene cation; Low-valent main-group chemistry.