Silyl methallylsulfinates: efficient and powerful agents for the chemoselective silylation of alcohols, polyols, phenols and carboxylic acids

Abstract

Alcohols, phenols and carboxylic acids are silylated with very good yields in the presence of silyl methallylsulfinates under non-basic conditions and with the formation of volatile co-products.

Palladium-catalyzed desulfinylative C–C allylation of Grignard reagents and enolates using allylsulfonyl chlorides and esters

“…[60][61][62][63][64] Neopentyl 1 H NMR spectra of the crude reaction mixtures, they were all better than 50%. In all cases the linear product 5a was favored (product of no allylic rearrangement).…”

Superparamagnetic iron oxide as an efficient and recoverable catalyst for rapid and selective trimethylsilyl protection of hydroxyl groups

“…[16,17] Many multistep syntheses and chemical transformations involve at least one step of hydroxyl group protection. [18,19] Conversion of alcohols into their corresponding silyl ethers is perhaps the most popular strategy for this purpose. [20] In this context, 1,1,1,3,3,3-hexamethyldisilazane (HMDS) has emerged as the most versatile reagent in recent years for trimethylsilyl (TMS) protection of alcohols and phenols.…”

Synthesis of allyl sulfoxides from allylsilanes via silyl sulfinates

“…24,25 Vogel's silyl sulfinates were also shown to silylate alcohols, phenols, and carboxylic acids. 26 This property has recently found application in the user-friendly derivatization and GC-analysis of non-volatile polyhydroxylated organic compounds. 27 Herein, we report the application of Vogel's silyl sulfinates, obtained from the sila-ene reaction between allylsilanes and sulfur dioxide (3+SO 2 ?4), in the synthesis of allyl sulfoxides (4?5, Scheme 2).…”