Ga(OTf)3-Catalyzed Temperature-Controlled Regioselective Friedel-Crafts Alkylation of Trifluoromethylated 3-Indolylmethanols with 2-Substituted Indoles: Divergent Synthesis of Trifluoromethylated Unsymmetrical 3,3'-and 3,6'-Bis(indolyl)methanes

Yuan Ling; Di An; Yuanyuan Zhou; Weidong Rao

doi:10.1021/acs.orglett.9b01135

Ga(OTf)₃-Catalyzed Temperature-Controlled Regioselective Friedel-Crafts Alkylation of Trifluoromethylated 3-Indolylmethanols with 2-Substituted Indoles: Divergent Synthesis of Trifluoromethylated Unsymmetrical 3,3'-and 3,6'-Bis(indolyl)methanes

Org Lett. 2019 May 3;21(9):3396-3401. doi: 10.1021/acs.orglett.9b01135. Epub 2019 Apr 22.

Authors

Yuan Ling¹, Di An¹, Yuanyuan Zhou¹, Weidong Rao¹

Affiliation

¹ Jiangsu Key Laboratory of Biomass-based Green Fuels and Chemicals, College of Chemical Engineering , Nanjing Forestry University , Nanjing 210037 , China.

PMID: 31008615
DOI: 10.1021/acs.orglett.9b01135

Abstract

An unprecedented Ga(OTf)₃-catalyzed, temperature-controlled regiodivergent alkylation of 2-substituted indoles with trifluoromethylated 3-indolylmethanols is described that provides structurally diverse unsymmetrical 3,3'- and 3,6'-bis(indolyl)methanes with a CF₃-containing quaternary carbon center in good to excellent yields under mild conditions. In addition, this present protocol could be successfully extended to the synthesis of difluoromethylated 3,3'- and 3,6'-bis(indolyl)methanes with excellent efficiency.

Publication types

Research Support, Non-U.S. Gov't