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Lewis/Brønsted acid-mediated cyclization/amidation of 1,6-enynes with nitriles: access to 3-enamide substituted dihydrobenzofurans.
Chem Commun (Camb). 2023 Apr 11; 59(30):4523-4526.CC

Abstract

A novel Lewis- and Brønsted-acid mediated electrophilic addition cyclization/amidation reaction of 1,6-enynes with nitriles to synthesize 3-enamide-substituted dihydrobenzofurans has been developed. The transformation involves the addition of a Brønsted acid as the electrophilic reagent to enynes, followed by intramolecular cyclization to form cationic intermediates, and the termination of the reaction by a nitrile as a nucleophile. The main features of the reaction include high atom economy and chemoselectivity, as well as the construction of C-C/C-N bonds in one step.

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Authors+Show Affiliations

Chen Z
Key Laboratory of Functional Molecular Engineering of Guangdong Province, State Key Laboratory of Luminescent Materials and Devices, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou, 510640, China. cewuwq@scut.edu.cn.
Huang W
Key Laboratory of Functional Molecular Engineering of Guangdong Province, State Key Laboratory of Luminescent Materials and Devices, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou, 510640, China. cewuwq@scut.edu.cn.
Su Y
Key Laboratory of Functional Molecular Engineering of Guangdong Province, State Key Laboratory of Luminescent Materials and Devices, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou, 510640, China. cewuwq@scut.edu.cn.
Jiang H
Key Laboratory of Functional Molecular Engineering of Guangdong Province, State Key Laboratory of Luminescent Materials and Devices, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou, 510640, China. cewuwq@scut.edu.cn.
Wu W
Key Laboratory of Functional Molecular Engineering of Guangdong Province, State Key Laboratory of Luminescent Materials and Devices, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou, 510640, China. cewuwq@scut.edu.cn.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

36975131

Citation

Chen, Zan, et al. "Lewis/Brønsted Acid-mediated Cyclization/amidation of 1,6-enynes With Nitriles: Access to 3-enamide Substituted Dihydrobenzofurans." Chemical Communications (Cambridge, England), vol. 59, no. 30, 2023, pp. 4523-4526.
Chen Z, Huang W, Su Y, et al. Lewis/Brønsted acid-mediated cyclization/amidation of 1,6-enynes with nitriles: access to 3-enamide substituted dihydrobenzofurans. Chem Commun (Camb). 2023;59(30):4523-4526.
Chen, Z., Huang, W., Su, Y., Jiang, H., & Wu, W. (2023). Lewis/Brønsted acid-mediated cyclization/amidation of 1,6-enynes with nitriles: access to 3-enamide substituted dihydrobenzofurans. Chemical Communications (Cambridge, England), 59(30), 4523-4526. https://doi.org/10.1039/d3cc00787a
Chen Z, et al. Lewis/Brønsted Acid-mediated Cyclization/amidation of 1,6-enynes With Nitriles: Access to 3-enamide Substituted Dihydrobenzofurans. Chem Commun (Camb). 2023 Apr 11;59(30):4523-4526. PubMed PMID: 36975131.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Lewis/Brønsted acid-mediated cyclization/amidation of 1,6-enynes with nitriles: access to 3-enamide substituted dihydrobenzofurans. AU - Chen,Zan, AU - Huang,Wenting, AU - Su,Yu, AU - Jiang,Huanfeng, AU - Wu,Wanqing, Y1 - 2023/04/11/ PY - 2023/3/29/medline PY - 2023/3/29/pubmed PY - 2023/3/28/entrez SP - 4523 EP - 4526 JF - Chemical communications (Cambridge, England) JO - Chem Commun (Camb) VL - 59 IS - 30 N2 - A novel Lewis- and Brønsted-acid mediated electrophilic addition cyclization/amidation reaction of 1,6-enynes with nitriles to synthesize 3-enamide-substituted dihydrobenzofurans has been developed. The transformation involves the addition of a Brønsted acid as the electrophilic reagent to enynes, followed by intramolecular cyclization to form cationic intermediates, and the termination of the reaction by a nitrile as a nucleophile. The main features of the reaction include high atom economy and chemoselectivity, as well as the construction of C-C/C-N bonds in one step. SN - 1364-548X UR - https://www.unboundmedicine.com/medline/citation/36975131/Lewis/Br��nsted_acid_mediated_cyclization/amidation_of_16_enynes_with_nitriles:_access_to_3_enamide_substituted_dihydrobenzofurans_ DB - PRIME DP - Unbound Medicine ER -
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