Palladium-catalyzed reaction of o-alkynyltrifluoroacetanilides with 1-bromoalkynes. An approach to 2-substituted 3-alkynylindoles and 2-substituted 3-acylindoles

Antonio Arcadi; Sandro Cacchi; Giancarlo Fabrizi; Fabio Marinelli; Luca M Parisi

doi:10.1021/jo050517z

Palladium-catalyzed reaction of o-alkynyltrifluoroacetanilides with 1-bromoalkynes. An approach to 2-substituted 3-alkynylindoles and 2-substituted 3-acylindoles

J Org Chem. 2005 Aug 5;70(16):6213-7. doi: 10.1021/jo050517z.

Authors

Antonio Arcadi¹, Sandro Cacchi, Giancarlo Fabrizi, Fabio Marinelli, Luca M Parisi

Affiliation

¹ Dipartimento di Chimica Ingegneria Chimica e Materiali della Facoltà di Scienze, Università di L'Aquila, Via Vetoio, Coppito Due, I-67100 L'Aquila, Italy.

PMID: 16050679
DOI: 10.1021/jo050517z

Abstract

The palladium-catalyzed reaction of o-alkynyltrifluoroacetanilides with 1-bromoalkynes affords free N-H 2-substituted 3-alkynylindoles in satisfactory to high yield. 2-Substituted 3-alkynylindoles revealed useful intermediates for the regioselective synthesis of 2-substituted 3-acylindoles. The latter can be prepared from o-alkynyltrifluoroacetanilides and 1-bromoalkynes via a one-pot cyclization-hydration protocol, omitting the isolation of 2-substituted 3-alkynylindoles.