An aqueous and recyclable copper(i)-catalyzed route to α-sulfenylated carbonyl compounds from propargylic alcohols and aryl thiols
A highly efficient one-step copper(i)-catalyzed method for the synthesis of α-sulfenylated carbonyl compounds from propargylic alcohols and aryl thiols in aqueous media is described. A variety of α-sulfenylated carbonyl compounds can be synthesized in good to excellent yields. The catalyst has been successfully recycled up to 4 times without any loss of activity in an aqueous medium.
Watile, Rahul A.,Biswas, Srijit,Samec, Joseph S. M.
supporting information
p. 3176 - 3179
(2013/11/06)
Atom-efficient gold(I)-chloride-catalyzed synthesis of α-sulfenylated carbonyl compounds from propargylic alcohols and aryl thiols: Substrate scope and experimental and theoretical mechanistic investigation
Gold(I)-chloride-catalyzed synthesis of α-sulfenylated carbonyl compounds from propargylic alcohols and aryl thiols showed a wide substrate scope with respect to both propargylic alcohols and aryl thiols. Primary and secondary aromatic propargylic alcohol
Biswas, Srijit,Dahlstrand, Christian,Watile, Rahul A.,Kalek, Marcin,Himo, Fahmi,Samec, Joseph S. M.
supporting information
p. 17939 - 17950
(2014/01/17)
A gold(I)-catalyzed route to α-sulfenylated carbonyl compounds from propargylic alcohols and aryl thiols
A one-step atom efficient gold(i)-catalyzed route to α-sulfenylated ketones and aldehydes from propargylic alcohols and aryl thiols is described.
Biswas, Srijit,Samec, Joseph S. M.
supporting information; experimental part
p. 6586 - 6588
(2012/07/28)
Amino-protecting groups subject to deblocking under conditions of nucleophilic addition to a Michael acceptor. Structure-Reactivity studies and use of the 2-(tert-Butylsulfonyl)-2-propenyloxycarbonyl (Bspoc) group
A new type of amino-protecting group is described in which a Michael acceptor is incorporated into the protectant so that treatment with a nucleophile will trigger deblocking. Comparison of various Michael acceptors showed that for several key electron-withdrawing groups, the order of reactivity was C6H5SO2 > Me3CSO2 > COOEt > C6H5SO > C6H4NO2-p. The reactivity of the nucleophile (e.g., primary and secondary aliphatic amines) followed an order related to both intrinsic basicity and steric effects. β- Substituents in the Michael acceptor caused significant retardation of the deblocking process. The Bspoc function was chosen for initial elaboration into a practical system for use in peptide synthesis. Bspoc amino acid chlorides were used as coupling agents and silica-tethered secondary amines as deblocking agents. With the latter, deblocking occurs cleanly and no byproducts remain in the organic solvent in which the deblocking is executed.
Carpino, Louis A.,Philbin, Michael
p. 4315 - 4323
(2007/10/03)
A Novel Synthesis of 3,4-Dihydro-2H-1-benzothiopyrans. Acid-Catalyzed Intermolecular Cycloaddition of Acetylenic Alcohols with Arenethiols
Reaction of the acetylenic alcohols with arenethiols in the presence of p-toluenesulfonic acid (p-TsOH) gave 3,4-dihydro-2H-1-benzothiopyrans (thiochromans) in good to excellent yields, the reaction of which may involve intermolecular cycloaddition via ca