Douglas, James J. published the artcileA Visible-Light-Mediated Radical Smiles Rearrangement and its Application to the Synthesis of a Difluoro-Substituted Spirocyclic ORL-1 Antagonist, Computed Properties of 254749-11-6, the publication is Angewandte Chemie, International Edition (2015), 54(49), 14898-14902, database is CAplus and MEDLINE.
In the presence of Ru(bpy)3Cl2 (bpy = 2,2′-bipyridine), 2-bromo-2,2-difluoroethyl arylsulfonates (and a styrenesulfonate) such as bromodifluoroethoxysulfonylthiophenecarboxylate I underwent chemoselective photochem. Smiles rearrangements mediated by Bu3 and HCO2H in DMSO to yield β-aryl-β,β-difluoroethanols such as II in 24-94% yields; a pyridinesulfonate and a chloropyrazolesulfonate were ineffective substrates in the photochem. Smiles rearrangement. Using the method, I was converted to the ORL-1 receptor antagonist III•HCl in five steps; the photochem. step could be conducted on 15 g scale using 0.01 mol% of the ruthenium catalyst, and the overall route compares favorably to the current synthetic sequence for III. The bromodifluoroethyl esters were prepared in two steps from Et bromodifluoroacetate via reduction to 2-bromo-2,2-difluoroethanol which was prepared on 40 g scale. 2-Bromo-2,2-difluoroethanol is volatile and a lachrymator and should be handled in a hood, and the photochem. Smiles rearrangements generate toxic SO2 gas as a byproduct.
Angewandte Chemie, International Edition published new progress about 254749-11-6. 254749-11-6 belongs to chlorides-buliding-blocks, auxiliary class Chloride,Nitrile,Benzene, name is 2-Chloro-4-cyanobenzene-1-sulfonyl chloride, and the molecular formula is C7H3Cl2NO2S, Computed Properties of 254749-11-6.
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