title: Hydrocarbon Soluble Recyclable Silylation Reagents and Purification Auxiliaries.
abstract: 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.
authors.affiliation: Department of Chemistry, Texas A&M University , College Station, Texas 77842-3012, United States.
authors.forename: Chih-Gang
authors.initials: CG
authors.lastname: Chao
authors.affiliation: Department of Chemistry, Texas A&M University , College Station, Texas 77842-3012, United States.
authors.forename: Ashley M
authors.initials: AM
authors.lastname: Leibham
authors.affiliation: Department of Chemistry, Texas A&M University , College Station, Texas 77842-3012, United States.
authors.forename: David E
authors.initials: DE
authors.lastname: Bergbreiter