Hydrocarbon Soluble Recyclable Silylation Reagents and Purification Auxiliaries. Academic Article

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

• Bergbreiter, David

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

publisher

• American Chemical Society (ACS)  Publisher

published in

• Organic Letters  Journal

keywords

• 0305 Organic Chemistry

PubMed Central ID

• 26911488

Digital Object Identifier (DOI)

• 10.1021/acs.orglett.6b00263

start page

• 1214

end page

• 1216

volume

• 18

issue

• 5

URL

• http%3A%2F%2Fdx.doi.org%2F10.1021%2Facs.orglett.6b00263