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- W4313596208 abstract "Abstract Trifluoromethyl‐bearing 5‐membered rings are prevalent in bioactive molecules, but modular approaches to these compounds by functionalization of robust C(sp 3 )−H bonds in a direct and selective manner are extremely challenging. Herein we report the rhodium‐catalyzed α‐CF 3 ‐α‐alkyl carbene insertion into C(sp 3 )−H bonds of a broad range of substrates to access 7 types of CF 3 ‐bearing saturated 5‐membered carbo‐ and heterocycles. The reaction is particularly effective for benzylic C−H insertion exerting good site‐, diastereo‐ and enantiocontrol, and applicable to the synthesis of chiral CF 3 analogues of bioactive molecules. Ruthenium α‐CF 3 ‐α‐alkyl carbene complexes underwent stoichiometric reactions to give C−H insertion products, lending evidence for the involvement of metal α‐CF 3 ‐α‐alkyl carbene species in the catalytic cycle. DFT calculations revealed that the π⋅⋅⋅π attraction and intra‐carbene C−H⋅⋅⋅F hydrogen bond elucidate the origin of selectivity of the benzylic C−H insertion reactions." @default.
- W4313596208 created "2023-01-06" @default.
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- W4313596208 date "2023-01-24" @default.
- W4313596208 modified "2023-10-01" @default.
- W4313596208 title "A Convergent, Modular Approach to Trifluoromethyl‐Bearing 5‐Membered Rings via Catalytic C(sp<sup>3</sup>)−H Activation" @default.
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- W4313596208 doi "https://doi.org/10.1002/ange.202215891" @default.
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