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Tosylhydrazone reduction mechanism

tosylhydrazone reduction mechanism

In a one-pot synthesis of optically active -hydroxy sulfones, intermediate -keto sulfones obtained via a nucleophilic substitution reaction of -bromoketones and sodium sulfinates were reduced through Ru-catalyzed asymmetric transfer hydrogenation using hcoona as a hydrogen source.
Formamide is a superior solvent for obtaining high yields.
A practical, rapid, and efficient microwave (MW) promoted nucleophilic substitution of alkyl halides or tosylates with alkali azides, thiocyanates or sulfinates in aqueous media tolerates various reactive functional groups.
N -bromosuccinimide and triphenylphosphine, followed by addition of sodium arenesulfinate with a catalytic amount of tetrabutylammonium iodide to afford the aryl sulfones in good to high yields.This mild transformation in an aqueous medium provides chiral -hydroxy sulfones with high yields and excellent enantioselectivities.A cross-coupling reaction between sulfonyl hydrazides and diazo compounds provides various -carbonyl sulfones in good yields.Kuhakarn, Synthesis, 2012,.An efficient one-pot multistep strategy comprising auto-oxidative difunctionalization of alkenes, oxidation of sulfides, and a further reduction of peroxides enables the synthesis of complex -hydroxysulfone derivatives from thiophenols and alkenes.

The addition of Grignard reagents or organolithium reagents to the SO2-surrogate dabso generates a diverse set of metal sulfinates, which can be trapped in situ with a wide range of C-electrophiles, including alkyl, allyl, and benzyl halides, epoxides, and (hetero)aryliodoniums to give sulfone products.
TosMIC acts as the sulfonylating agent initiated by a Cu(OTf)2-catalyzed hydration to form a formamide intermediate, which undergoes facile C-S bond cleavage under the mediation of Cs2CO3.
Related An efficient cobalt-catalyzed reductive coupling reaction of alkyl halides with alkenes bearing electron-withdrawing pronostic gagnant com groups in the presence of water and zinc powder in acetonitrile epson promo rewards gave the corresponding Michael-type addition products in high yields.
A Zn/CuI-mediated coupling of alkyl halides with vinyl sulfones, vinyl sulfonates, and vinyl sulfonamides is described.Chem., 2006, 71, 655-658.Kuhakarn, Synthesis, 2017,.The photoredox catalyst fac Ir(ppy)3 enables the synthesis of -hydroxysulfones from sulfonyl chlorides and styrenes in the presence of water by a visible light mediated atom transfer radical addition (atra)-like process.IR experiments revealed that pyridine not only acts as a base to successfully surpress atra (atom transfer radical addition) process, but also plays a vital role in reducing the activity of sulfinic acids.The reaction provides -keto- and -hydroxy sulfones in a simple and reliable way through a sulfa-Michael reaction that proceeds with good yield and chemoselectivity.An oxidation-free method provides sulfinic acids and sulfinate salts from easily prepared sulfone-substituted benzothiazole derivatives under mild reaction conditions.

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