Hydrocarbon Soluble Recyclable Silylation Reagents and Purification Auxiliaries. Academic Article uri icon


  • Procedures using heptane-phase-selectively soluble octadecyldimethylsilyl groups to facilitate separations and silyl reagent regeneration are described. These results show that alcohols and alkynes protected by these groups are phase-selectively soluble in hydrocarbon solvents. In a thermomorphic cyclohexane/DMF system, >96% of the silylated alcohols are in the cyclohexane phase, allowing these compounds to be purified by a simple liquid/liquid extraction. Applications of these silylating agents in a Grignard synthesis and Sonogashira reaction are described.

published proceedings

  • Org Lett

author list (cited authors)

  • Chao, C., Leibham, A. M., & Bergbreiter, D. E.

citation count

  • 6

complete list of authors

  • Chao, Chih-Gang||Leibham, Ashley M||Bergbreiter, David E

publication date

  • March 2016