Journal
TETRAHEDRON
Volume 75, Issue 30, Pages 4017-4023Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2019.06.031
Keywords
Benzamides; Organochalcogen; Cross-coupling; Copper
Categories
Funding
- Fundacao de Amparo a Pesquisa do Estado do Rio Grande do Sul [PRONEM 16/2551-0000240-1]
- Conselho Nacional de Desenvolvimento Cientifico e Tecnologico [428193/2018-8]
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This work describes the copper-catalyzed Csp-chalcogen bond formation through cross-coupling reactions of propynylbenzamides and diorganyl dichalcogenides at room temperature, under open atmosphere. Generally, the reactions have proceeded very smoothly, affording the new class of organochalcogen-containing propynylbenzamides in good yields. Notably, this protocol showed to be tolerant to neutral, electron-donating and electron-withdrawing substituents present in both reaction substrates. In addition, the applicability of the carbon-chalcogen bond as a reactive site has been proved by successfully employment of the N-methyl-N-(3-(butylselanyl)prop-2-yn-1-yl)benzamide as a precursor in palladium-catalyzed Suzuki and Sonogashira type reactions. (C) 2019 Elsevier Ltd. All rights reserved.
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