103603-55-0Relevant articles and documents
Sulfoxide-directed metal-free ortho-propargylation of aromatics and heteroaromatics
Eberhart, Andrew J.,Shrives, Harry J.,álvarez, Estela,Carr?r, Amandine,Zhang, Yuntong,Procter, David J.
, p. 7428 - 7434 (2015)
Abstract A sulfoxide-directed, metal-free ortho-propargylation of aromatics and heteroaromatics exploits intermolecular delivery of a propargyl nucleophile to sulfur followed by an intramolecular relay to carbon. The operationally simple cross-coupling procedure is general, regiospecific with regard to the propargyl nucleophile, and shows complete selectivity for products of ortho-propargylation over allenylation. The use of secondary propargyl silanes allows metal-free ortho-coupling to form carbon-carbon bonds between aromatic and heteroaromatic rings and secondary propargylic centres. The 'safety-catch' nature of the sulfoxide directing group is illustrated in a selective, iterative double cross-coupling process. The products of propargylation are versatile intermediates and they have been readily converted into substituted benzothiophenes. A sulfoxide-directed, metal-free ortho-propargylation of aromatics and heteroaromatics exploits intermolecular delivery of a propargyl nucleophile to sulfur followed by an intramolecular relay to carbon (see scheme). The process allows metal-free ortho-coupling to form carbon-carbon bonds between aromatic and heteroaromatic rings and propargylic centres.
Sulfur(IV)-mediated transformations: From ylide transfer to metal-free arylation of carbonyl compounds
Huang, Xueliang,Patil, Mahendra,Fares, Christophe,Thiel, Walter,Maulide, Nuno
, p. 7312 - 7323 (2013/06/26)
The development of a direct ylide transfer to carbonyl derivatives and of a sulfoxide-mediated arylation is presented from a unified perspective. Mechanistic studies (including density functional calculations) support a common reaction pathway and showcase how subtle changes in reactant properties can lead to disparate and seemingly unrelated reaction outcomes.
Reduction of sulfoxides to sulfides mediated by ferrocene and trifluoroacetic anhydride
Kobayashi, Kenji,Kubota, Yasuo,Furukawa, Naomichi
, p. 400 - 401 (2007/10/03)
The reaction of diaryl sulfoxides with trifluoroacetic anhydride in the presence of ferrocene gives the corresponding sulfide. The reduction of sulfoxides composed of the ferrocene-spacer-methylsulfinyl triad system would proceed via a through-bond electron transfer rather than a through-space process.
