This method demonstrates enantioselective synthesis of diarylindolylmethanes via Friedel–Crafts alkylation, highlighting ortho-quinone methide involvement.
We report an efficient Lewis acid catalyzed enantioselective synthesis of diarylindolylmethanes via in situ generated ortho-quinone methides. The protocol enables selective Friedel-Crafts alkylation at indole C3, and by blocking this site, extends selectively to C2 position. Mechanistic studies, including quantum calculations and Hammett analysis, reveal selectivity arising from β-methide steric hindrance and catalyst-substrate π-π interactions. This method provides broad substrate scope, high yields, excellent functional group tolerance, and access to complex indole derivatives.
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Lee et al. (2025) studied this question.
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