A Selectfluor-promoted oxidative reaction of disulfides and amines: access to sulfinamides
An unprecedented transition-metal-free oxidative reaction of disulfides and amines with Selectfluor as a mild oxidant under aerobic conditions was developed. This reaction was conducted under mild conditions and tolerated a wide range of coupling partners including disulfides and amines, affording the corresponding sulfinamide products in good chemical yields. Furthermore, this reaction could be used in gram-scale synthesis. This reaction enriches the research content of Selectfluor and provides a valuable vista for the convenient synthesis of sulfinamides.
A New, Practical One-Pot Synthesis of Unprotected Sulfonimidamides by Transfer of Electrophilic NH to Sulfinamides
Unprotected tertiary sulfonimidamides have been prepared in good to excellent yields in a one-pot transformation from tertiary sulfinamides through NH transfer. The reaction is mediated by commercially available (diacetoxyiodo)benzene and ammonium carbamate in methanol under convenient conditions. A wide range of functional groups are tolerated and initial results indicate that the NH transfer is stereospecific. A small molecule X-ray analysis of NH sulfonimidamide 2 a and its behavior in selected in vitro assays in comparison to the matched sulfonamide are also reported. This new reaction provides a safe, short and efficient approach to sulfonimidamides, which have been the subject of recent, growing interest in the life sciences.
Tert-Butyl Sulfoxide as a Starting Point for the Synthesis of Sulfinyl Containing Compounds
Sulfoxides bearing a tert-butyl group can be activated using N-bromosuccinimide (NBS) under acidic conditions and then subsequently treated with a variety of nitrogen, carbon, or oxygen nucleophiles to afford a wide range of the corresponding sulfinic acid amides, new sulfoxides, and sulfinic acid esters.
Wei, Juhong,Sun, Zhihua
p. 5396 - 5399
(2015/11/18)
Fast and efficient synthesis of sulfinamides by the oxidation of sulfenamides using potassium fluoride and m-chloroperoxybenzoic acid
A procedure for the synthesis of N-alkyl-, N-cycloalkyl-, N,N-dialkyl-, and N-arylarenesulfinamides from the corresponding sulfenamides using KF/m-chloroperoxybenzoic acid (CPBA) in CH3CN-H2O is described. High efficiency (fast react
Datta, Mrityunjoy,Buglass, Alan J.
experimental part
p. 1760 - 1769
(2012/05/04)
Expedient synthesis of sulfinamides from sulfonyl chlorides
Sulfinamides were synthesized from sulfonyl chlorides using a procedure involving in situ reduction of sulfonyl chlorides. The reaction is broad in scope and easy to perform.
Harmata, Michael,Zheng, Pinguan,Huang, Chaofeng,Gomes, Maria G.,Ying, Weijiang,Ranyanil, Kanok-On,Balan, Gayatri,Calkins, Nathan L.
p. 683 - 685
(2007/10/03)
Ligand Exchange Reaction of Sulfoxides in Organic Synthesis: A New Synthesis of α-Chloroketones from Carbonyl Compounds with One-Carbon Homologation
A new procedure for one-carbon homologation of carbonyl compounds to α-chloroketones is described.Addition of the carbanion of dichloromethyl phenyl sulfoxide with ketones and aldehydes gave the adducts, chloro alcohols, in good yields.Treatment of the chloro alcohols with EtMgBr or lithium diisopropylamide gave one-carbon homologated α-chloroketones via β-oxido carbenoid rearrangement in moderate to good yields.One-carbon homologation of esters to α-chloroketones was realized via the ligand exchange reaction of the sulfinyl group of α-chloro α-sulfinyl ketones, which were synthesized from methyl esters and chloromethyl phenyl sulfoxide, with EtMgBr.
Satoh Tsuyoshi,Mizu, Yasuhiro,Kawashima, Taku,Yamakawa, Koji
p. 703 - 710
(2007/10/02)
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