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Palladium-catalyzed sequential oxidative cyclization/coupling of 2-alkynylphenols and alkenes: a direct entry into 3-alkenylbenzofurans.
Org Lett. 2009 Mar 05; 11(5):1083-6.OL

Abstract

A new Pd-catalyzed tandem intramolecular oxypalladation/Heck-type coupling between 2-alkynylphenols and alkenes is reported, leading to 3-(1-alkenyl)benzofurans. Participating alkenes include those substituted with an electron-withdrawing group (ester, ketone, amide, nitrile, sulfone), as well as styrene. Remarkably, beta-substituted-alpha,beta-unsaturated carbonyl-type derivatives also participate effectively. The ready availability of substituted alkynylphenols, together with flexibility in the alkene choice, makes this simple strategy a versatile one for the synthesis of structurally diverse benzofuran derivatives.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Martínez C
Departamento de Química Orgánica, Facultad de Química, Universidade de Vigo, Lagoas-Marcosende s/n, 36310 Vigo, Spain.
Alvarez R
No affiliation info available
Aurrecoechea JM
No affiliation info available

MeSH

AlkenesAlkynesBenzofuransCatalysisCyclizationMolecular StructureOxidation-ReductionPalladiumPhenols

Pub Type(s)

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

Language

eng

PubMed ID

19199489

Citation

Martínez, Claudio, et al. "Palladium-catalyzed Sequential Oxidative Cyclization/coupling of 2-alkynylphenols and Alkenes: a Direct Entry Into 3-alkenylbenzofurans." Organic Letters, vol. 11, no. 5, 2009, pp. 1083-6.
Martínez C, Alvarez R, Aurrecoechea JM. Palladium-catalyzed sequential oxidative cyclization/coupling of 2-alkynylphenols and alkenes: a direct entry into 3-alkenylbenzofurans. Org Lett. 2009;11(5):1083-6.
Martínez, C., Alvarez, R., & Aurrecoechea, J. M. (2009). Palladium-catalyzed sequential oxidative cyclization/coupling of 2-alkynylphenols and alkenes: a direct entry into 3-alkenylbenzofurans. Organic Letters, 11(5), 1083-6. https://doi.org/10.1021/ol8028687
Martínez C, Alvarez R, Aurrecoechea JM. Palladium-catalyzed Sequential Oxidative Cyclization/coupling of 2-alkynylphenols and Alkenes: a Direct Entry Into 3-alkenylbenzofurans. Org Lett. 2009 Mar 5;11(5):1083-6. PubMed PMID: 19199489.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Palladium-catalyzed sequential oxidative cyclization/coupling of 2-alkynylphenols and alkenes: a direct entry into 3-alkenylbenzofurans. AU - Martínez,Claudio, AU - Alvarez,Rosana, AU - Aurrecoechea,José M, PY - 2009/2/10/entrez PY - 2009/2/10/pubmed PY - 2010/8/25/medline SP - 1083 EP - 6 JF - Organic letters JO - Org Lett VL - 11 IS - 5 N2 - A new Pd-catalyzed tandem intramolecular oxypalladation/Heck-type coupling between 2-alkynylphenols and alkenes is reported, leading to 3-(1-alkenyl)benzofurans. Participating alkenes include those substituted with an electron-withdrawing group (ester, ketone, amide, nitrile, sulfone), as well as styrene. Remarkably, beta-substituted-alpha,beta-unsaturated carbonyl-type derivatives also participate effectively. The ready availability of substituted alkynylphenols, together with flexibility in the alkene choice, makes this simple strategy a versatile one for the synthesis of structurally diverse benzofuran derivatives. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/19199489/Palladium_catalyzed_sequential_oxidative_cyclization/coupling_of_2_alkynylphenols_and_alkenes:_a_direct_entry_into_3_alkenylbenzofurans_ L2 - https://doi.org/10.1021/ol8028687 DB - PRIME DP - Unbound Medicine ER -