Novel aromatic fluoroolefins via fluoro-Julia-Kocienski olefination
Fluoroolefins, which play an increasingly important role as peptide mimics in pharmaceuticals and as crop protection agents, are generated using a fluoro-Julia-Kocienski olefination. Their preparation can easily be accomplished using a Mitsunobu reaction and subsequent oxidation to generate the required benzothiazolyl sulfones. The key step of this process was the electrophilic -fluorination of the sulfone with N-fluorobenzenesulfonimide. The last stage of the successful synthesis of the fluoroolefins was the modified Julia-Kocienski olefination under basic conditions. Further functionalization was followed with the application of a Suzuki reaction. Georg Thieme Verlag Stuttgart.
Allendoerfer, Nadine,Es-Sayed, Mazen,Nieger, Martin,Braese, Stefan
experimental part
p. 3439 - 3448
(2010/12/19)
A mild, efficient method for the synthesis of aromatic and aliphatic sulfonamides
A two-step method was developed for the synthesis of aromatic and aliphatic sulfonamides from the corresponding sulfinates using bis(2,2,2-trichloroethyl)azodicarboxylate as the electrophilic nitrogen source. The intermediate sulfonylhydrazides were obtained in very good yields and were cleaved under reductive conditions to deliver the desired sulfonamides. A variety of substituents in the aromatic ring are well tolerated as well as heterocycles.
Chan, Wing Yan,Berthelette, Carl
p. 4537 - 4540
(2007/10/03)
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