Tags

Type your tag names separated by a space and hit enter

Sequential and one-pot reactions of phenols with bromoalkynes for the synthesis of (Z)-2-bromovinyl phenyl ethers and benzo[b]furans.
Org Lett. 2011 Nov 18; 13(22):5968-71.OL

Abstract

Benzo[b]furans were prepared in one pot based on the addition/palladium-catalyzed C-H bond functionalization of phenols with bromoalkynes. The addition reactions of phenols to bromoalkynes generated (Z)-2-bromovinyl phenyl ethers in high yields with excellent regio- and stereoselectivity. The obtained (Z)-2-bromovinyl phenyl ethers subsequently proceeded by intramolecular cyclization to afford 2-substituted benzo[b]furans in good yields through palladium-catalyzed direct C-H bond functionalizations. It is important to note that the transformation of phenols with bromoalkynes into benzo[b]furans could be carried out in one pot with a simple and efficient tandem procedure.

Links

Publisher Full Text (DOI)

Authors+Show Affiliations

Wang S
Department of Chemistry, Huaibei Normal University, Huaibei, Anhui 235000, PR China.
Li P
No affiliation info available
Yu L
No affiliation info available
Wang L
No affiliation info available

MeSH

AlkynesBenzofuransBromineCyclizationMolecular StructurePalladiumPhenolsPhenyl EthersVinyl Compounds

Pub Type(s)

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

Language

eng

PubMed ID

22007879

Citation

Wang, Shihua, et al. "Sequential and One-pot Reactions of Phenols With Bromoalkynes for the Synthesis of (Z)-2-bromovinyl Phenyl Ethers and Benzo[b]furans." Organic Letters, vol. 13, no. 22, 2011, pp. 5968-71.
Wang S, Li P, Yu L, et al. Sequential and one-pot reactions of phenols with bromoalkynes for the synthesis of (Z)-2-bromovinyl phenyl ethers and benzo[b]furans. Org Lett. 2011;13(22):5968-71.
Wang, S., Li, P., Yu, L., & Wang, L. (2011). Sequential and one-pot reactions of phenols with bromoalkynes for the synthesis of (Z)-2-bromovinyl phenyl ethers and benzo[b]furans. Organic Letters, 13(22), 5968-71. https://doi.org/10.1021/ol202383z
Wang S, et al. Sequential and One-pot Reactions of Phenols With Bromoalkynes for the Synthesis of (Z)-2-bromovinyl Phenyl Ethers and Benzo[b]furans. Org Lett. 2011 Nov 18;13(22):5968-71. PubMed PMID: 22007879.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Sequential and one-pot reactions of phenols with bromoalkynes for the synthesis of (Z)-2-bromovinyl phenyl ethers and benzo[b]furans. AU - Wang,Shihua, AU - Li,Pinhua, AU - Yu,Lin, AU - Wang,Lei, Y1 - 2011/10/18/ PY - 2011/10/20/entrez PY - 2011/10/20/pubmed PY - 2012/2/22/medline SP - 5968 EP - 71 JF - Organic letters JO - Org Lett VL - 13 IS - 22 N2 - Benzo[b]furans were prepared in one pot based on the addition/palladium-catalyzed C-H bond functionalization of phenols with bromoalkynes. The addition reactions of phenols to bromoalkynes generated (Z)-2-bromovinyl phenyl ethers in high yields with excellent regio- and stereoselectivity. The obtained (Z)-2-bromovinyl phenyl ethers subsequently proceeded by intramolecular cyclization to afford 2-substituted benzo[b]furans in good yields through palladium-catalyzed direct C-H bond functionalizations. It is important to note that the transformation of phenols with bromoalkynes into benzo[b]furans could be carried out in one pot with a simple and efficient tandem procedure. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/22007879/Sequential_and_one_pot_reactions_of_phenols_with_bromoalkynes_for_the_synthesis_of__Z__2_bromovinyl_phenyl_ethers_and_benzo[b]furans_ L2 - https://doi.org/10.1021/ol202383z DB - PRIME DP - Unbound Medicine ER -