Convenient synthesis of 2-alkynylbenzazoles through Sonogashira cross-coupling reaction between thioethers and terminal alkynes

[Display omitted] We describe herein the synthesis of 2-alkynylbenzoxazole and 2-alkynylbenzothiazole derivatives through the Sonogashira cross-coupling reaction of the corresponding thioethers and terminal alkynes under aerobic conditions, using CuI and Pd(dppf)Cl2 as catalysts. The synthetic metho...

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Published inTetrahedron letters Vol. 56; no. 39; pp. 5349 - 5352
Main Authors Paun, Anca, Matache, Mihaela, Enache, Florina, Nicolau, Ioana, Paraschivescu, Codruta C., Ionita, Petre, Zarafu, Irina, Parvulescu, Vasile I., Guillaumet, Gérald
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 23.09.2015
Elsevier
Subjects
Benzoxazole
Chemistry
Chemistry, Organic
Cross-coupling reactions
Heteroaromatic thioethers
Palladium-catalysis
Physical Sciences
Science & Technology
Sonogashira reaction
Heteroaromatic thioethers
Cross-coupling reactions
Sonogashira reaction
Benzoxazole
Palladium-catalysis
ANALOGS
INHIBITORS
DIRECT ALKYNYLATION
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Summary:[Display omitted] We describe herein the synthesis of 2-alkynylbenzoxazole and 2-alkynylbenzothiazole derivatives through the Sonogashira cross-coupling reaction of the corresponding thioethers and terminal alkynes under aerobic conditions, using CuI and Pd(dppf)Cl2 as catalysts. The synthetic methodology allows the convenient cross-coupling of heteroaromatic substrates with a wide variety of aromatic and aliphatic alkynes, in moderate to good yields. The behavior of mercapto benzoxazoles and benzothiazoles were also investigated in the desulfitative Sonogashira cross-coupling reaction. It is noteworthy that the reaction occurred better under aerobic conditions rather than an inert atmosphere, although with increased amounts of the diyne side-product.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2015.08.001