Synthesis of Benzo[ b ]thiophenes via Electrophilic Sulfur Mediated Cyclization of Alkynylthioanisoles.

Autor:	Alikhani Z; Department of Chemistry, University of West Florida, 11000 University Pkwy, Pensacola, Florida 32514, United States., Albertson AG; Department of Chemistry, University of West Florida, 11000 University Pkwy, Pensacola, Florida 32514, United States., Walter CA; Department of Chemistry, University of West Florida, 11000 University Pkwy, Pensacola, Florida 32514, United States., Masih PJ; Department of Biology, University of West Florida, 11000 University Pkwy, Pensacola, Florida 32514, United States., Kesharwani T; Department of Chemistry, University of West Florida, 11000 University Pkwy, Pensacola, Florida 32514, United States.
Jazyk:	angličtina
Zdroj:	The Journal of organic chemistry [J Org Chem] 2022 May 06; Vol. 87 (9), pp. 6312-6320. Date of Electronic Publication: 2022 Apr 18.
DOI:	10.1021/acs.joc.1c02606
Abstrakt:	A stable dimethyl(thiodimethyl)sulfonium tetrafluoroborate salt was employed for the electrophilic cyclization reaction of o -alkynyl thioanisoles for the synthesis of 2,3-disubstituted benzo[ b ]thiophenes. The reaction described herein works well with various substituted alkynes in excellent yields, and a valuable thiomethyl group was introduced with ease. The reaction utilizes moderate reaction conditions and ambient temperature while tolerating various functionalities. To elucidate the mechanism, electrophilic addition reactions using the dimethyl(thiodimethyl)sulfonium tetrafluoroborate salt with diphenylacetylene was demonstrated.
Databáze:	MEDLINE
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