82239-64-3Relevant articles and documents
A practical and chemoselective Mo-catalysed sulfoxide reduction protocol using a 3-mercaptopropyl-functionalized silica gel (MPS)
García, Nuria,Fernández-Rodríguez, Manuel A.,García-García, Patricia,Pedrosa, María R.,Arnáiz, Francisco J.,Sanz, Roberto
, p. 27083 - 27086 (2016/03/25)
A convenient sulfoxide deoxygenation procedure using a mercaptopropyl-functionalized silica gel as the reducing agent is described. This new protocol based on a heterogeneous reagent displays broad scope and tolerance to reducible functional groups and, from an experimental point of view, enhances previous methods by simplifying the isolation of the sulfide to a simple filtration.
Pinacol as a new green reducing agent: Molybdenum-catalyzed chemoselective reduction of sulfoxides and nitroaromatics
Garcia, Nuria,Garcia-Garcia, Patricia,Fernandez-Rodriguez, Manuel A.,Rubio, Ruben,Pedrosa, Maria R.,Arnaiz, Francisco J.,Sanz, Roberto
supporting information; experimental part, p. 321 - 327 (2012/04/11)
Pinacol is disclosed as a new chemoselective and environmentally benign reducing agent for sulfoxides and nitroaromatics assisted by readily available dichlorodioxomolybdenum(VI) complexes as catalysts. A wide range of substrates including those bearing challenging functional groups has been efficiently and selectively reduced with acetone and water being the only by-products of these reactions. Copyright
Tin Radical Addition to Alkynyl Sulfides: Reactivity of the Intermediate Thioalkyl-Substituted β-(Tributylstannyl)vinyl Radicals
Capella, Laura,Montevecchi, Pier Carlo,Nanni, Daniele
, p. 3368 - 3374 (2007/10/02)
Phenyl and benzyl alkynyl sulfides 1a-g and 3a, phenylalkynylamines 19a,b, ethers 22a,b, and selenide 31 reacted with tributyltin radicals to give intermediate β-stannylvinyl radicals, whose fate depended on the nature of the side chain. 4-Phenylthio-substituted but-1-en-2-yl radicals underwent stereospecific 5-exo cyclization on the adjacent phenyl ring.The resulting spirocyclohexadienyl radicals gave thiophenes and thiopyrans by carbon-sulfur bond scission or ring expansion on the exocyclic double bond, respectively.Similar behavior was exhibited by the corresponding selenium-containing radical, which afforded a selenophene almost exclusively. (Benzylthio)alkyl-substituted radicals gave products deriving from intramolecular SH2 substitution at the sulfur atom, whereas propargyl sulfides yielded a stannylallene via a β-scission reaction.No 6(or more)-membered ring closure was observed with pentynyl and hexynyl phenyl sulfides 1b,c, which gave only the (E)-addition products of tin hydride; oxygen- and nitrogen-containing vinyl radicals also gave the (E)-adducts exclusively.An interaction between the unpaired electron orbital and the empty low-energy orbitals of the heteroatom might explain why sulfur and selenium can undergo 5-exo cyclization.