75421-79-3Relevant academic research and scientific papers
Nitrosoarene-catalyzed regioselective aromatic C-H sulfinylation with thiols under aerobic conditions
Chatterjee, Indranil,Patel, Sandeep,Pradhan, Suman
supporting information, p. 5054 - 5057 (2020/05/18)
Aromatic amines and (hetero)arenes, such as indoles and pyrroles, are regioselectively sulfinylated under mild aerobic conditions using nitrosoarenes as a redox-catalyst. The nitrosoarene is involved in the electron transfer process with arenes to generate a crucial arene radical cation intermediate for C-H sulfinylation. The present methodology requires no directing group, can be scaled up easily and is applicable for the late-stage functionalization of drug molecules and natural products with high regioselectivity.
Asymmetric oxidation of 2-(arylsulfenyl)pyrroles
Thompson, Alison,Garabatos-Perera, Jose R.,Gillis, H. Martin
, p. 676 - 681 (2008/12/21)
The asymmetric oxidation of prochiral 2-(arylsulfenyl)pyrroles has been investigated. A marked electronic effect within the substrate significantly influenced the degree of enantioselectivitv obtained, with very high enantio-selectivity being obtained for
Comparison of benzene, nitrobenzene, and dinitrobenzene 2-arylsulfenylpyrroles
Garabatos-Perera, Jose R.,Rotstein, Benjamin H.,Thompson, Alison
, p. 7382 - 7385 (2008/02/11)
(Chemical Equation Presented) The effectiveness of the 2,4- dinitrobenzenesulfenyl and 4-nitrobenzenesulfenyl groups as masking and directing groups at the 2-position of pyrrole has been investigated and compared to that of 2-phenylthiopyrrole. The presen
Synthesis and Rearrangement of 2-(Arylsulfinyl)- and 2-(Alkylsulfinyl)pyrroles
Carmona, Olga,Greenhouse, Robert,Landeros, Rosita,Muchowski, Joseph M.
, p. 5336 - 5339 (2007/10/02)
Pyrrole and N-methylpyrrole reacted with aryl- and alkylsulfinyl chlorides, at 0 deg C, to give the corresponding 2-sulfinylpyrroles as the major products only when contact of the products with the liberated hydrogen chloride was minimized or eliminated.If this precaution was not taken, the 3-sulfinylpyrroles were the principle products.In contrast, N-(phenylsulfinyl)succinimide (2a) reacted, at room temperature, with a variety of pyrroles to produce the 2-phenylsulfinyl compounds in good yields.The 2-(arylsulfinyl)- and 2-(alkylsulfinyl)pyrroles undergo a remarkably facile acid-promoted rearrangement to the isomeric 3-sulfinylpyrroles.This transposition is, at least in part, an intermolecular process as demonstrated by crossover experiments.
