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Synthesis of 2,3-disubstituted benzo[b]furans by the palladium-catalyzed coupling of o-iodoanisoles and terminal alkynes, followed by electrophilic cyclization.
J Org Chem. 2005 Dec 09; 70(25):10292-6.JO

Abstract

[reaction: see text] 2,3-Disubstituted benzo[b]furans are readily prepared under very mild reaction conditions by the palladium/copper-catalyzed cross-coupling of various o-iodoanisoles and terminal alkynes, followed by electrophilic cyclization with I2, PhSeCl, or p-O2NC6H4SCl. Aryl- and vinylic-substituted alkynes undergo electrophilic cyclization in excellent yields. Biologically important furopyridines can be prepared by this approach in high yields.

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Authors+Show Affiliations

Yue D
Department of Chemistry, Iowa State University, Ames, Iowa 50011, USA.
Yao T
No affiliation info available
Larock RC
No affiliation info available

MeSH

AlkynesAnisolesBenzofuransCatalysisCyclizationPalladium

Pub Type(s)

Journal Article
Research Support, N.I.H., Extramural

Language

eng

PubMed ID

16323837

Citation

Yue, Dawei, et al. "Synthesis of 2,3-disubstituted Benzo[b]furans By the Palladium-catalyzed Coupling of O-iodoanisoles and Terminal Alkynes, Followed By Electrophilic Cyclization." The Journal of Organic Chemistry, vol. 70, no. 25, 2005, pp. 10292-6.
Yue D, Yao T, Larock RC. Synthesis of 2,3-disubstituted benzo[b]furans by the palladium-catalyzed coupling of o-iodoanisoles and terminal alkynes, followed by electrophilic cyclization. J Org Chem. 2005;70(25):10292-6.
Yue, D., Yao, T., & Larock, R. C. (2005). Synthesis of 2,3-disubstituted benzo[b]furans by the palladium-catalyzed coupling of o-iodoanisoles and terminal alkynes, followed by electrophilic cyclization. The Journal of Organic Chemistry, 70(25), 10292-6.
Yue D, Yao T, Larock RC. Synthesis of 2,3-disubstituted Benzo[b]furans By the Palladium-catalyzed Coupling of O-iodoanisoles and Terminal Alkynes, Followed By Electrophilic Cyclization. J Org Chem. 2005 Dec 9;70(25):10292-6. PubMed PMID: 16323837.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Synthesis of 2,3-disubstituted benzo[b]furans by the palladium-catalyzed coupling of o-iodoanisoles and terminal alkynes, followed by electrophilic cyclization. AU - Yue,Dawei, AU - Yao,Tuanli, AU - Larock,Richard C, PY - 2005/12/6/pubmed PY - 2006/6/15/medline PY - 2005/12/6/entrez SP - 10292 EP - 6 JF - The Journal of organic chemistry JO - J Org Chem VL - 70 IS - 25 N2 - [reaction: see text] 2,3-Disubstituted benzo[b]furans are readily prepared under very mild reaction conditions by the palladium/copper-catalyzed cross-coupling of various o-iodoanisoles and terminal alkynes, followed by electrophilic cyclization with I2, PhSeCl, or p-O2NC6H4SCl. Aryl- and vinylic-substituted alkynes undergo electrophilic cyclization in excellent yields. Biologically important furopyridines can be prepared by this approach in high yields. SN - 0022-3263 UR - https://www.unboundmedicine.com/medline/citation/16323837/Synthesis_of_23_disubstituted_benzo[b]furans_by_the_palladium_catalyzed_coupling_of_o_iodoanisoles_and_terminal_alkynes_followed_by_electrophilic_cyclization_ DB - PRIME DP - Unbound Medicine ER -