1-Trifluoromethylisoquinolines from α-Benzylated Tosylmethyl Isocyanide Derivatives in a Modular Approach

Wang, Lin; Studer, Armido

1-Trifluoromethylisoquinolines from α-Benzylated Tosylmethyl Isocyanide Derivatives in a Modular Approach

2017

Wang, Lin | Studer, Armido

The preparation of various 1-trifluoromethylisoquinolines from α-benzylated tosylmethyl isocyanide derivatives and the commercial Togni reagent using a radical cascade is reported. The starting isocyanides are readily prepared in a modular sequence from commercial tosylmethyl isocyanide via sequential double α-alkylation, and the radical reaction proceeds under mild conditions with high efficiency without any transition-metal catalyst via electron catalysis. This valuable protocol has been successfully applied to the total synthesis of CF₃-mansouramycin B.

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