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Catalytic Nitrene Transfer To Alkynes: A Novel and Versatile Route for the Synthesis of Sulfinamides and Isothiazoles
Author(s) -
Rodríguez Manuel R.,
Beltrán Álvaro,
Mudarra Ángel L.,
Álvarez Eleuterio,
Maseras Feliu,
DíazRequejo M. Mar,
Pérez Pedro J.
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201705664
Subject(s) - nitrene , chemistry , tosyl , moiety , sulfoxide , catalysis , alkyne , sulfone , imine , combinatorial chemistry , ring (chemistry) , polymer chemistry , medicinal chemistry , stereochemistry , organic chemistry
A novel transformation is reported for the reaction of terminal or internal alkynes with the nitrene precursor PhI=NTs (Ts= p ‐toluenesulfonyl) in the presence of catalytic amounts of Tp Br3 Cu(NCMe) (Tp Br3 =hydrotris(3,4,5‐tribromo‐pyrazolylborate). Two products containing an imine functionality have been isolated from the reaction mixtures, identified as sulfinamides and isothiazoles. The former correspond to the formal reduction of the sulfone group into sulfoxide, whereas the latter involves the insertion of an alkyne carbon atom into the aromatic ring of the N ‐tosyl moiety.