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Palladium-catalyzed oxidative cyclization of 3-phenoxyacrylates: an approach to construct substituted benzofurans from phenols.
J Org Chem. 2011 Jun 03; 76(11):4692-6.JO

Abstract

In this paper, a novel and applicable synthesis of benzofurans from commercially available phenols and propiolate through the direct oxidative cyclization has been developed. In the presence of Pd(OAc)(2)/PPh(3) and CF(3)CO(2)Ag, (E)-type 3-phenoxyacrylates underwent reaction smoothly to generate the corresponding benzofurans in good yields in benzene at 110 °C under the air pressure. In addition, this transformation of phenols into benzofurans can also be carried out in one pot. The process was simple and efficient. A tentative mechanism of palladium-catalyzed oxidative cyclization of 3-phenoxyacrylates was proposed.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Li C
Department of Chemistry, Huaibei Normal University, Huaibei, Anhui, P R China.
Zhang Y
No affiliation info available
Li P
No affiliation info available
Wang L
No affiliation info available

MeSH

AcrylatesBenzofuransCatalysisCyclizationOxidation-ReductionPalladiumPhenols

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

21542613

Citation

Li, Chengliang, et al. "Palladium-catalyzed Oxidative Cyclization of 3-phenoxyacrylates: an Approach to Construct Substituted Benzofurans From Phenols." The Journal of Organic Chemistry, vol. 76, no. 11, 2011, pp. 4692-6.
Li C, Zhang Y, Li P, et al. Palladium-catalyzed oxidative cyclization of 3-phenoxyacrylates: an approach to construct substituted benzofurans from phenols. J Org Chem. 2011;76(11):4692-6.
Li, C., Zhang, Y., Li, P., & Wang, L. (2011). Palladium-catalyzed oxidative cyclization of 3-phenoxyacrylates: an approach to construct substituted benzofurans from phenols. The Journal of Organic Chemistry, 76(11), 4692-6. https://doi.org/10.1021/jo200317f
Li C, et al. Palladium-catalyzed Oxidative Cyclization of 3-phenoxyacrylates: an Approach to Construct Substituted Benzofurans From Phenols. J Org Chem. 2011 Jun 3;76(11):4692-6. PubMed PMID: 21542613.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Palladium-catalyzed oxidative cyclization of 3-phenoxyacrylates: an approach to construct substituted benzofurans from phenols. AU - Li,Chengliang, AU - Zhang,Yicheng, AU - Li,Pinhua, AU - Wang,Lei, Y1 - 2011/05/04/ PY - 2011/5/6/entrez PY - 2011/5/6/pubmed PY - 2011/9/21/medline SP - 4692 EP - 6 JF - The Journal of organic chemistry JO - J Org Chem VL - 76 IS - 11 N2 - In this paper, a novel and applicable synthesis of benzofurans from commercially available phenols and propiolate through the direct oxidative cyclization has been developed. In the presence of Pd(OAc)(2)/PPh(3) and CF(3)CO(2)Ag, (E)-type 3-phenoxyacrylates underwent reaction smoothly to generate the corresponding benzofurans in good yields in benzene at 110 °C under the air pressure. In addition, this transformation of phenols into benzofurans can also be carried out in one pot. The process was simple and efficient. A tentative mechanism of palladium-catalyzed oxidative cyclization of 3-phenoxyacrylates was proposed. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/21542613/Palladium_catalyzed_oxidative_cyclization_of_3_phenoxyacrylates:_an_approach_to_construct_substituted_benzofurans_from_phenols_ L2 - https://doi.org/10.1021/jo200317f DB - PRIME DP - Unbound Medicine ER -