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.
Nucleophilic ortho-propargylation of aryl sulfoxides: An interrupted pummerer/allenyl thio-Claisen rearrangement sequence
Eberhart, Andrew J.,Procter, David J.
supporting information, p. 4008 - 4011 (2013/05/21)
A new direction: The nucleophilic ortho-propargylation of aryl sulfoxides exploits intermolecular delivery of the nucleophile to sulfur followed by an intramolecular relay to carbon (see scheme). The simple, metal-free procedure is general, regiospecific with regard to the propargyl nucleophile, and completely selective for products of ortho-propargylation over allenylation.
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.