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Literature DB >> 23883393

Mild and general palladium-catalyzed synthesis of methyl aryl ethers enabled by the use of a palladacycle precatalyst.

Abstract

A general method for the Pd-catalyzed coupling of methanol with (hetero)aryl halides is described. The reactions proceed under mild conditions with a wide range of aryl and heteroaryl halides to give methyl aryl ethers in high yield.

Entities: Chemical

Mesh：

Substances：

Year: 2013 PMID： 23883393 PMCID： PMC3776604 DOI： 10.1021/ol401796v

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

19 in total

1. Metachromins U-W: cytotoxic merosesquiterpenoids from an Australian specimen of the sponge Thorecta reticulata.

Authors: Simon P B Ovenden; Jonathan L Nielson; Catherine H Liptrot; Richard H Willis; Dianne M Tapiolas; Anthony D Wright; Cherie A Motti
Journal: J Nat Prod Date: 2011-04-22 Impact factor: 4.050

2. A convenient and practical synthesis of anisoles and deuterated anisoles by palladium-catalyzed coupling reactions of aryl bromides and chlorides.

Authors: Saravanan Gowrisankar; Helfried Neumann; Matthias Beller
Journal: Chemistry Date: 2012-02-01 Impact factor: 5.236

3. Big interest in heavy drugs.

Authors: Katharine Sanderson
Journal: Nature Date: 2009-03-19 Impact factor: 49.962

4. The selective reaction of aryl halides with KOH: synthesis of phenols, aromatic ethers, and benzofurans.

Authors: Kevin W Anderson; Takashi Ikawa; Rachel E Tundel; Stephen L Buchwald
Journal: J Am Chem Soc Date: 2006-08-23 Impact factor: 15.419

5. A single phosphine ligand allows palladium-catalyzed intermolecular C-O bond formation with secondary and primary alcohols.

Authors: Xiaoxing Wu; Brett P Fors; Stephen L Buchwald
Journal: Angew Chem Int Ed Engl Date: 2011-09-12 Impact factor: 15.336

6. Copper-catalyzed coupling of aryl iodides with aliphatic alcohols.

Authors: Martina Wolter; Gero Nordmann; Gabriel E Job; Stephen L Buchwald
Journal: Org Lett Date: 2002-03-21 Impact factor: 6.005

7. An Improved Synthesis of BrettPhos and RockPhos-Type Biarylphosphine Ligands.

Authors: Naoyuki Hoshiya; Stephen L Buchwald
Journal: Adv Synth Catal Date: 2012-06-27 Impact factor: 5.837

8. Synthesis and application of palladium precatalysts that accommodate extremely bulky di-tert-butylphosphino biaryl ligands.

Authors: Nicholas C Bruno; Stephen L Buchwald
Journal: Org Lett Date: 2013-05-15 Impact factor: 6.005

9. An improved Cu-based catalyst system for the reactions of alcohols with aryl halides.

Authors: Ryan A Altman; Alexandr Shafir; Alice Choi; Phillip A Lichtor; Stephen L Buchwald
Journal: J Org Chem Date: 2007-11-29 Impact factor: 4.354

10. Extraction of essential oil and pigments from Curcuma longa [L] by steam distillation and extraction with volatile solvents.

Authors: Anna Carolina C M Manzan; Fabio S Toniolo; Eliane Bredow; Nanci P Povh
Journal: J Agric Food Chem Date: 2003-11-05 Impact factor: 5.279

10 in total

1. Monophosphine Ligands Promote Pd-Catalyzed C-S Cross-Coupling Reactions at Room Temperature with Soluble Bases.

Authors: Jessica Xu; Richard Y Liu; Charles S Yeung; Stephen L Buchwald
Journal: ACS Catal Date: 2019-06-21 Impact factor: 13.084

2. Well-defined nickel and palladium precatalysts for cross-coupling.

Authors: Nilay Hazari; Patrick R Melvin; Megan Mohadjer Beromi
Journal: Nat Rev Chem Date: 2017-03-01 Impact factor: 34.035

3. Oxidative Addition Complexes as Precatalysts for Cross-Coupling Reactions Requiring Extremely Bulky Biarylphosphine Ligands.

Authors: Bryan T Ingoglia; Stephen L Buchwald
Journal: Org Lett Date: 2017-05-12 Impact factor: 6.005

Mild and general palladium-catalyzed synthesis of methyl aryl ethers enabled by the use of a palladacycle precatalyst.

1. Metachromins U-W: cytotoxic merosesquiterpenoids from an Australian specimen of the sponge Thorecta reticulata.

2. A convenient and practical synthesis of anisoles and deuterated anisoles by palladium-catalyzed coupling reactions of aryl bromides and chlorides.

3. Big interest in heavy drugs.

4. The selective reaction of aryl halides with KOH: synthesis of phenols, aromatic ethers, and benzofurans.

5. A single phosphine ligand allows palladium-catalyzed intermolecular C-O bond formation with secondary and primary alcohols.

6. Copper-catalyzed coupling of aryl iodides with aliphatic alcohols.

7. An Improved Synthesis of BrettPhos and RockPhos-Type Biarylphosphine Ligands.

8. Synthesis and application of palladium precatalysts that accommodate extremely bulky di-tert-butylphosphino biaryl ligands.

9. An improved Cu-based catalyst system for the reactions of alcohols with aryl halides.

10. Extraction of essential oil and pigments from Curcuma longa [L] by steam distillation and extraction with volatile solvents.

1. Monophosphine Ligands Promote Pd-Catalyzed C-S Cross-Coupling Reactions at Room Temperature with Soluble Bases.

2. Well-defined nickel and palladium precatalysts for cross-coupling.

3. Oxidative Addition Complexes as Precatalysts for Cross-Coupling Reactions Requiring Extremely Bulky Biarylphosphine Ligands.

4. Improved Process for the Palladium-Catalyzed C-O Cross-Coupling of Secondary Alcohols.

5. Ligand Promoted meta-C-H Chlorination of Anilines and Phenols.

6. Palladium-Catalyzed C-O Cross-Coupling of Primary Alcohols.

7. Oxalohydrazide Ligands for Copper-Catalyzed C-O Coupling Reactions with High Turnover Numbers.

8. Palladium-catalyzed hydroxylation of aryl and heteroaryl halides enabled by the use of a palladacycle precatalyst.

9. Chemoselective, Scalable Nickel-Electrocatalytic O-Arylation of Alcohols.

10. Esterification of Aryl/Alkyl Acids Catalysed by N-bromosuccinimide under Mild Reaction Conditions.