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- W2893847084 abstract "Catalytic C–C bond cleavage processes followed by further transformations are some of the most fascinating reactions in chemistry and valuable organic synthesis tools. Herein, we demonstrate that the regioselectivity of C–C bond cleavage in 1-azabiphenylene and its derivatives can be switched by using neutral or cationic transition metal catalysts. The use of the former leads to selective distal C–C bond cleavage (with respect to the position of the nitrogen atom), whereas use of the latter leads to selective proximal bond cleavage. This process enables synthesis of a variety of complex heterocycles by regioselective C–C bond cleavage switched on demand. Density functional theory calculations (SMD/M06/DGDZVP level of theory) show that the regioselectivity is a result of kinetically controlled oxidative addition into the C–C bond. In neutral complexes the transition states (TS) for distal cleavage have lower energy, in agreement with experiments. For the cationic catalyst, the proximal TSs are stabilized presumably by relieving the Cl–N dipole–dipole repulsion when the Rh-bound Cl is removed whereas the distal TSs remain largely unaffected." @default.
- W2893847084 created "2018-10-05" @default.
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- W2893847084 date "2018-09-24" @default.
- W2893847084 modified "2023-10-03" @default.
- W2893847084 title "Catalyst-Counterion Controlled, Regioselective C–C Bond Cleavage in 1-Azabiphenylene: Synthesis of Selectively Substituted Benzoisoquinolines" @default.
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- W2893847084 doi "https://doi.org/10.1021/acscatal.8b01874" @default.
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