α-Fluoromethylarenes are common substructures in pharmaceuticals and agrochemicals, with the introduction of fluorine often resulting in improved biological activity and stability. Despite recent progress, synthetic routes to α-fluorinated diarylmethanes are still rare. Herein we describe the Pd-catalyzed Suzuki-Miyaura cross-coupling of α-fluorinated benzylic triflones with arylboronic acids affording structurally diverse α-fluorinated diarylmethanes. The ease of synthesis of fluorinated triflones as the key starting materials enables powerful late-stage transformations of known biologically active compounds into fluorinated analogs.
A new method for the generation of tertiary radicals thorugh single electron reduction of alkylsulfones promoted by Zn and 1,9-phenanthlorine has been developed. These radicals could be employed in the...
The
desulfonylative radical addition of tertiary alkyl groups to gem-difluoroalkenes by photoredox Ir-catalyst is described.
This method exhibits broad substrate scope, affording structurally
diverse (E)-fluoroalkene derivatives in a highly
stereoselective manner. The resulting (E)-fluoroalkenes
were converted into complex fused cyclic compounds by intramolecular
cyclization reactions. Control experiments and theoretical calculations
are consistent with a single Ir catalyst playing the dual role of
generating radical species from sulfones via single electron transfer
and mediating Z/E isomerization via energy transfer.
A subset of fluoroalkenes provided Z stereoisomers
with >90% selectivity, but the same alkenes could also be obtained
as E isomers with high selectivity by taking advantage
of a secondary Z to E photoisomerization.
A new method for the synthesis of benzhydryl amines from the reaction of readily available sulfone derivatives with amines is described. The Cu‐catalyzed desulfonylative amination not only provides structurally diverse benzhydryl amines in good yields, but is also applicable to iterative and intramolecular aminations. Control experiments suggested that the formation of a Cu‐carbene intermediate generated from the sulfone substrate, which represents a new route for desulfonylative transformations.
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