Solvent-Free and Efficient Synthesis of Silatranes <i>via</i> an Organocatalytic Protocol under Mild Conditions
Myong Joon Oh, Ireneusz Kownacki, Maciej Kubicki
Abstract
High Resolution Image Download MS PowerPoint Slide The organocatalytic approach to the formation of silatranyl cages permitted the design of a solvent-free and efficient protocol for the preparation of various organosilatranes. We discovered that amidine derivatives efficiently catalyze the conversion of trialkoxysilanes into organosilatranes, and their catalytic activity is related to the p K BH+ values. NMR studies of equimolar reactions of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) and 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) with selected substrates allowed proposing a reliable scheme for the transesterification process and silatranyl cage formation. In addition, green chemistry metrics for the scaled-up synthesis of vinylsilatrane ( 3k ) were appointed. Finally, a scheme for the industrial production of silatrane derivatives with DBU and solvent regeneration was proposed, supported by a catalyst recycling experiment.