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Arylation of Olefins with N-Unprotected Bromobisindole Ethanamines: Expanding the Scope of the Mizoroki–Heck Reaction

Year: 2026

Type: article

Abstract: High Resolution Image Download MS PowerPoint Slide A protecting-group-free Mizoroki–Heck arylation of olefins with N-unprotected bromobisindole ethanamines and, more generally, N-unprotected heterocyclic electrophiles is described. Efficient palladium-catalyzed coupling is achieved through appropriate base selection: CsF is optimal for substrates bearing intrinsic basic sites, whereas 1-decylamine is required. The method tolerates a wide range of styrenes, heteroaryl olefins, acrylates, and N-containing substrates, including unprotected tryptamines, anilines, and haloindole derivatives. Its practicality is also demonstrated by the synthesis of the natural product trans -resveratrol.

Source: The Journal of Organic Chemistry

DOI: 10.1021/acs.joc.6c00302

Authors: Alessandro Buono, Lorenzo Mariani, Martina Chiappini, Andrea Duranti, Diego Olivieri, Simone Lucarini

Institution: University of Urbino

Language: English

Topic: Catalytic Cross-Coupling Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,500

Funders: European Commission, Università degli Studi di Urbino Carlo Bo, Ministero dell'Università e della Ricerca, NextGenerationEU