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Silver-Mediated Synthesis of Substituted Benzofuran- and Indole-Pyrroles via Sequential Reaction of ortho-Alkynylaromatics with Methylene Isocyanides
KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry. Jiangsu Normal Univ, Jiangsu Key Lab Green Synth Funct Mat, Sch Chem & Mat Sci, Xuzhou 221116, Jiangsu, Peoples R China.ORCID iD: 0000-0002-5533-2075
KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry.
KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry.ORCID iD: 0000-0002-6089-5454
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2019 (English)In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 84, no 14, p. 8998-9006Article in journal (Refereed) Published
Abstract [en]

A silver-mediated reaction between 2-ethynyl-3-(1-hydroxyprop-2-yn-1-yl)phenols or 2-ethyn-yl-3-(1-hydroxy-prop-2-yn-1-yl)anilines and methylene isocyanides has been developed. A sequential 5-endo-dig cyclization and [3 + 2] cycloaddition process is proposed. This synthetic strategy is atom- and step-efficient and applicable to a broad scope of substrates, allowing the synthesis of valuable substituted benzofuran- and indole-pyrroles in moderate to high yields.

Place, publisher, year, edition, pages
American Chemical Society (ACS), 2019. Vol. 84, no 14, p. 8998-9006
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Chemical Sciences
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URN: urn:nbn:se:kth:diva-255747DOI: 10.1021/acs.joc.9b00528ISI: 000476957000015PubMedID: 31117557Scopus ID: 2-s2.0-85067067190OAI: oai:DiVA.org:kth-255747DiVA, id: diva2:1341831
Note

QC 20190812

Available from: 2019-08-12 Created: 2019-08-12 Last updated: 2019-08-12Bibliographically approved

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Shatskiy, AndreyKärkäs, Markus D.

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