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Simple amine/Pd(OAc)(2)-catalyzed suzuki coupling reactions of aryl bromides under mild aerobic conditions.
J Org Chem. 2004 Jun 25; 69(13):4330-5.JO

Abstract

A new palladium catalyst (DAPCy) made from Pd(OAc)(2) and commercially available, inexpensive dicyclohexylamine has been developed for the Suzuki coupling reaction of aryl bromides with boronic acids to give the coupling products in good to high yields. The air-stable catalyst was characterized and well-defined by X-ray crystallography. A catalytic system involving DAPCy in dioxane demonstrates a temperature-dependent reactivity toward aryl bromides with different electronic substituents, and selectively couples electron-deficient aryl bromides with boronic acids over electron-rich ones at room temperature. Another catalytic system employing DAPCy in EtOH provides a general and convenient method to prepare biaryls from aryl bromides and boronic acids with a broad range of functional groups at room temperature and under aerobic conditions.

Authors+Show Affiliations

Tao B
Department of Chemistry, MSC 8L0378, Georgia State University, 33 Gilmer Street, SE Unit 8, Atlanta, Georgia 30303-3088, USA.
Boykin DW
No affiliation info available

MeSH

AminesBoronic AcidsCatalysisHydrocarbons, AromaticHydrocarbons, BrominatedLigandsModels, MolecularMolecular StructurePalladium

Pub Type(s)

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

Language

eng

PubMed ID

15202886

Citation

Tao, Bin, and David W. Boykin. "Simple amine/Pd(OAc)(2)-catalyzed Suzuki Coupling Reactions of Aryl Bromides Under Mild Aerobic Conditions." The Journal of Organic Chemistry, vol. 69, no. 13, 2004, pp. 4330-5.
Tao B, Boykin DW. Simple amine/Pd(OAc)(2)-catalyzed suzuki coupling reactions of aryl bromides under mild aerobic conditions. J Org Chem. 2004;69(13):4330-5.
Tao, B., & Boykin, D. W. (2004). Simple amine/Pd(OAc)(2)-catalyzed suzuki coupling reactions of aryl bromides under mild aerobic conditions. The Journal of Organic Chemistry, 69(13), 4330-5.
Tao B, Boykin DW. Simple amine/Pd(OAc)(2)-catalyzed Suzuki Coupling Reactions of Aryl Bromides Under Mild Aerobic Conditions. J Org Chem. 2004 Jun 25;69(13):4330-5. PubMed PMID: 15202886.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Simple amine/Pd(OAc)(2)-catalyzed suzuki coupling reactions of aryl bromides under mild aerobic conditions. AU - Tao,Bin, AU - Boykin,David W, PY - 2004/6/19/pubmed PY - 2005/4/14/medline PY - 2004/6/19/entrez SP - 4330 EP - 5 JF - The Journal of organic chemistry JO - J Org Chem VL - 69 IS - 13 N2 - A new palladium catalyst (DAPCy) made from Pd(OAc)(2) and commercially available, inexpensive dicyclohexylamine has been developed for the Suzuki coupling reaction of aryl bromides with boronic acids to give the coupling products in good to high yields. The air-stable catalyst was characterized and well-defined by X-ray crystallography. A catalytic system involving DAPCy in dioxane demonstrates a temperature-dependent reactivity toward aryl bromides with different electronic substituents, and selectively couples electron-deficient aryl bromides with boronic acids over electron-rich ones at room temperature. Another catalytic system employing DAPCy in EtOH provides a general and convenient method to prepare biaryls from aryl bromides and boronic acids with a broad range of functional groups at room temperature and under aerobic conditions. SN - 0022-3263 UR - https://www.unboundmedicine.com/medline/citation/15202886/Simple_amine/Pd_OAc__2__catalyzed_suzuki_coupling_reactions_of_aryl_bromides_under_mild_aerobic_conditions_ DB - PRIME DP - Unbound Medicine ER -