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One-pot synthesis of substituted benzo[b]furans from mono- and dichlorophenols using palladium catalysts bearing dihydroxyterphenylphosphine.
J Org Chem. 2013 Sep 20; 78(18):9270-81.JO

Abstract

A dihydroxyterphenylphosphine bearing cyclohexyl groups on the phosphorus atom (Cy-DHTP) was found to be a powerful ligand for the palladium-catalyzed one-pot synthesis of substituted benzo[b]furans from 2-chlorophenols and terminal alkynes. This catalyst system was also applicable to the sequential one-pot synthesis of disubstituted benzo[b]furans from dichlorophenols via the Suzuki-Miyaura cross-coupling of chlorobenzo[b]furan with boronic acids. The use of two ligands, Cy-DHTP and XPhos, is the key to promoting the reactions. Mechanistic studies suggest that the Pd-Cy-DHTP catalyst is the active species in the Sonogashira cross-coupling step, while the Pd-XPhos catalyst accelerates the Suzuki-Miyaura cross-coupling step.

Authors+Show Affiliations

School of Pharmaceutical Sciences, University of Shizuoka , 52-1 Yada, Suruga-ku, Shizuoka 422-8526, Japan.No affiliation info availableNo affiliation info available

Pub Type(s)

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

Language

eng

PubMed ID

23952238

Citation

Yamaguchi, Miyuki, et al. "One-pot Synthesis of Substituted Benzo[b]furans From Mono- and Dichlorophenols Using Palladium Catalysts Bearing Dihydroxyterphenylphosphine." The Journal of Organic Chemistry, vol. 78, no. 18, 2013, pp. 9270-81.
Yamaguchi M, Katsumata H, Manabe K. One-pot synthesis of substituted benzo[b]furans from mono- and dichlorophenols using palladium catalysts bearing dihydroxyterphenylphosphine. J Org Chem. 2013;78(18):9270-81.
Yamaguchi, M., Katsumata, H., & Manabe, K. (2013). One-pot synthesis of substituted benzo[b]furans from mono- and dichlorophenols using palladium catalysts bearing dihydroxyterphenylphosphine. The Journal of Organic Chemistry, 78(18), 9270-81. https://doi.org/10.1021/jo401503t
Yamaguchi M, Katsumata H, Manabe K. One-pot Synthesis of Substituted Benzo[b]furans From Mono- and Dichlorophenols Using Palladium Catalysts Bearing Dihydroxyterphenylphosphine. J Org Chem. 2013 Sep 20;78(18):9270-81. PubMed PMID: 23952238.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - One-pot synthesis of substituted benzo[b]furans from mono- and dichlorophenols using palladium catalysts bearing dihydroxyterphenylphosphine. AU - Yamaguchi,Miyuki, AU - Katsumata,Haruka, AU - Manabe,Kei, Y1 - 2013/08/30/ PY - 2013/8/20/entrez PY - 2013/8/21/pubmed PY - 2014/3/1/medline SP - 9270 EP - 81 JF - The Journal of organic chemistry JO - J Org Chem VL - 78 IS - 18 N2 - A dihydroxyterphenylphosphine bearing cyclohexyl groups on the phosphorus atom (Cy-DHTP) was found to be a powerful ligand for the palladium-catalyzed one-pot synthesis of substituted benzo[b]furans from 2-chlorophenols and terminal alkynes. This catalyst system was also applicable to the sequential one-pot synthesis of disubstituted benzo[b]furans from dichlorophenols via the Suzuki-Miyaura cross-coupling of chlorobenzo[b]furan with boronic acids. The use of two ligands, Cy-DHTP and XPhos, is the key to promoting the reactions. Mechanistic studies suggest that the Pd-Cy-DHTP catalyst is the active species in the Sonogashira cross-coupling step, while the Pd-XPhos catalyst accelerates the Suzuki-Miyaura cross-coupling step. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/23952238/One_pot_synthesis_of_substituted_benzo[b]furans_from_mono__and_dichlorophenols_using_palladium_catalysts_bearing_dihydroxyterphenylphosphine_ L2 - https://doi.org/10.1021/jo401503t DB - PRIME DP - Unbound Medicine ER -