3-Silaazetidine: An Unexplored yet Versatile Organosilane Species for Ring Expansion toward Silaazacycles

Small-ring silacycles are important organosilane species in main-group chemistry and have found numerous applications in organic synthesis. 3-Silaazetidine, a unique small silacycle bearing silicon and nitrogen atoms, has not been adequately explored due to the lack of a general synthetic scheme and its sensitivity to air. Here, we describe that 3-silaazetidine can be easily prepared in situ from diverse air-stable precursors ((RSO2NHCH2SiR2CH2Cl)-C-1). 3-Silaazetidine shows excellent functional group tolerance in a palladium-catalyzed ring expansion reaction with terminal alkynes, giving 3-silatetrahydropyridines and diverse silaazacycle derivatives, which are promising ring frameworks for the discovery of Si-containing functional molecules.

Automated summary

The unique small silacycle 3-silaazetidine can be easily prepared in situ from diverse air-stable precursors and shows excellent functional group tolerance in a palladium-catalyzed ring expansion reaction, giving diverse silaazacycle derivatives. These derivatives are promising ring frameworks for the discovery of Si-containing functional molecules.