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Intermolecular cyclotrimerization of haloketoalkynes and internal alkynes: facile access to arenes and phthalides

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Abstract

A highly chemo- and regioselective cyclo(co)trimerization between 3-halopropiolamides and symmetrical internal alkynes is reported. The reaction is catalyzed by CpRuCl(COD) and proceeds under air at ambient temperature in ethanol with no additional precautions. Iodo-, bromo-, and chloropropiolamides, esters, and ketones are viable coupling partners and, in a 2 : 1 stoichiometry relative to internal alkyne, yield fully-substituted arenes in a single step. The highest regioselectivities (96% single isomer) were observed when employing 2° and 3°-halopropiolamides. A mechanistic hypothesis accounting for this selectivity is proposed. Notably, by using 1,4-butynediol as the internal alkyne, in situ lactonization following [2+2+2]-cycloaddition generates therapeutically-relevant phthalide pharmacophores directly.

Graphical abstract: Intermolecular cyclotrimerization of haloketoalkynes and internal alkynes: facile access to arenes and phthalides

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Article information


Submitted
21 Aug 2020
Accepted
05 Oct 2020
First published
05 Oct 2020

Chem. Commun., 2020, Advance Article
Article type
Communication

Intermolecular cyclotrimerization of haloketoalkynes and internal alkynes: facile access to arenes and phthalides

A. P. Silvestri and J. S. Oakdale, Chem. Commun., 2020, Advance Article , DOI: 10.1039/D0CC05706A

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