Rhodium(iii)-catalyzed C-H/C-F activation sequence: expedient and divergent synthesis of 2-benzylated indoles and 2,2′-bis(indolyl)methanes

Herein, an original and divergent synthetic method for fluorinated 2-benzylated indoles and 2,2 '-bis(indolyl)methanes has been established for the first time via Rh(iii)-catalyzed C-H/C-F activation of arenes employing 3,3-difluoro-2-exo-methylidene indolines as novel cross-coupling partners. This redox-neutral protocol exhibited a broad substrate scope (30 examples, up to 97% yield) and high functional-group compatibility. Gram-scale and mechanistic studies were also performed.

Automated summary

An original and divergent synthetic method for fluorinated 2-benzylated indoles and 2,2'-bis(indolyl)methanes has been established via Rh(iii)-catalyzed C-H/C-F activation, using 3,3-difluoro-2-exo-methylidene indolines as novel cross-coupling partners. This protocol demonstrated a broad substrate scope, high functional-group compatibility, and was further studied on gram-scale and mechanistically.