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Issue 4, 2017
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Sequential In-catalyzed intramolecular hydroarylation and Pd-catalyzed cross-coupling reactions using bromopropargyl aryl ethers and amines

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Abstract

A sequential one-pot indium-catalyzed intramolecular hydroarylation (IMHA) of bromopropargyl aryl ethers and amines, and palladium-catalyzed cross-coupling reaction using triorganoindium reagents (R3In) has been developed. In this transformation, the IMHA of 3-bromo-2-propynyl aryl ethers under indium(III) catalysis, proceeds regioselectively through a 6-endo dig pathway to afford 4-bromo-2H-chromenes. Subsequent palladium-catalyzed cross-coupling with R3In gives 4-substituted-2H-chromenes in one-pot. This sequential transformation was extended to 3-bromo-2-propynyl-N-tosylanilines to afford 4-substituted-1,2-dihydroquinolines. The dual-catalyzed procedure takes place efficiently with a variety of propargyl aryl ethers and amines and R3In (R = aryl, heteroaryl, alkyl or alkynyl), showing the efficiency of these organometallics and proving the compatibility of indium and palladium in catalysis.

Graphical abstract: Sequential In-catalyzed intramolecular hydroarylation and Pd-catalyzed cross-coupling reactions using bromopropargyl aryl ethers and amines

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Publication details

The article was received on 17 Nov 2016, accepted on 23 Dec 2016 and first published on 26 Dec 2016


Article type: Research Article
DOI: 10.1039/C6QO00721J
Citation: Org. Chem. Front., 2017,4, 500-505
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    Sequential In-catalyzed intramolecular hydroarylation and Pd-catalyzed cross-coupling reactions using bromopropargyl aryl ethers and amines

    L. Alonso-Marañón, L. A. Sarandeses, M. M. Martínez and J. Pérez Sestelo, Org. Chem. Front., 2017, 4, 500
    DOI: 10.1039/C6QO00721J

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