Catalytic Nitrene Transfer To Alkynes: A Novel and Versatile Route for the Synthesis of Sulfinamides and Isothiazoles
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 hav...
| Autores: | , , , , , , |
|---|---|
| Formato: | artículo |
| Fecha de publicación: | 2017 |
| País: | España |
| Recursos: | Universidad de Huelva (UHU) |
| Repositorio: | Arias Montano. Repositorio Institucional de la Universidad de Huelva |
| Idioma: | inglés |
| OAI Identifier: | oai:ariasmontano.uhu.es:10272/16196 |
| Acesso em linha: | http://hdl.handle.net/10272/16196 |
| Access Level: | acceso abierto |
| Palavra-chave: | Alkyne functionalization Copper catalysis Isothiazoles Nitrene transfer Sulfinamides |
| Resumo: | 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. |
|---|