Fe(III)/ l -Valine-Catalyzed One-Pot Synthesis of N -Sulfinyl- and N -Sulfonylimines via Oxidative Cascade Reaction of Alcohols with Sulfinamides or Sulfonamides
An efficient Fe(III), l -valine, and 4-OH-TEMPO catalytic system was found for the oxidation of alcohols followed by condensation with sulfinamide or sulfonamide in one pot for the synthesis of N -sulfinyl- and N- sulfonylimines compounds under mild conditions. This transformation accommodates a variety of substrates, shows high functional-group tolerance, and affords the corresponding products in good to excellent yields.
Direct synthesis of N-sulfinyl- and N-sulfonylimines via copper/l-proline-catalyzed aerobic oxidative cascade reaction of alcohols with sulfinamides or sulfonamides
An efficient one-pot synthetic method of N-sulfinyl- and N-sulfonylimines by the condensation of alcohols with sulfinamides or sulfonamides under mild and green conditions has been developed using a combination of CuI, l-proline and TEMPO. This system shows excellent functional group compatibility for a wide range of substrates and affords the corresponding products in good to excellent yields.
Halogenations of S-Benzyl-S-phenylsulfoximides and Base-induced Rearrangements of Their N- and α-Halo Derivatives to N-Sulfinylimines
The reactions of S-benzyl- and S-(p-nitrobenzyl)sulfoximides 1a, b with N-bromosuccinimide or tert-butyl hypochlorite gave the corresponding N-halosulfoximides 2a, b or 3a, b, respectively, in good yields.The N-bromo-S-(p-nitrobenzyl)sulfoximide 2b decomp
Thermolysis of α-Azido Sulfides, Sulfoxides, and Sulfones: Dependence of Mechanism on Oxidation State of Sulfur
Thermolyses of α-azidobenzyl phenyl sulfide (1), sulfoxide (3), and sulfone (2) proceed at markedly different rates.Sulfone 2 requires the highest temperature (> 150 deg C), whereas sulfide 1 loses nitrogen at 120 deg C with neighboring group participation by the sulfur atom to produce N-benzylidenebenzenesulfenamide 4 in 75percent yield.Sulfoxide 3 readily decomposes at 70 deg C through a radical-pair intermediate, which gives rise to a CIDNP effect in the reaction products.Kinetic data are presented supporting the suggested reaction mechanisms.
Jarvis, Bruce B.,Nicholas, Paul E.,Midiwo, Jacob O.
p. 3878 - 3882
(2007/10/02)
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