Hydrocarbon Soluble Recyclable Silylation Reagents and Purification Auxiliaries

Organic Letters
Chih-Gang ChaoD E Bergbreiter

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.

References

Feb 20, 2007·Chemical Reviews·Rafael Chinchilla, Carmen Najera
Feb 13, 2009·Chemical Reviews·David E BergbreiterChayanant Hongfa
Jan 13, 2010·The Journal of Organic Chemistry·David E Bergbreiter, Yun-Chin Yang
Jun 29, 2011·Organic Letters·Christopher HobbsDavid E Bergbreiter
Mar 13, 2014·Angewandte Chemie·Sachin HandaBruce H Lipshutz
Feb 5, 2016·Organic Letters·Yuki MatsunoKazuhiro Chiba

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Citations

Oct 19, 2016·Journal of the American Chemical Society·Mary L HarrellDavid E Bergbreiter

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