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

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

Research Abstract Table of Contents

Jump to the:

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

Kevin W Anderson,Takashi Ikawa,Rachel E Tundel,Stephen L Buchwald,

The direct and selective synthesis of phenols from aryl/heteroaryl halides and KOH has been achieved through the use of highly active monophosphine-based catalysts derived from Pd(2)dba(3) and ligands L1 or L2 and the biphasic solvent system 1,4-dioxane/H(2)O. We have also demonstrated a one-pot method of phenol formation/alkylation for the preparation of alkyl aryl ethers from aryl halides. In many instances, this protocol overcomes limitations in existing Pd-catalyzed coupling reactions of aliphatic alcohols with aryl halides. Finally, we demonstrate that substituted benzofurans can be prepared efficiently via a Pd-catalyzed phenol formation/cyclization protocol starting from 2-chloroaryl alkynes.

The selective reaction of aryl halides with KOH: synthesis of phenols, aromatic ethers, and benzofurans. Publishing Authors By Initials

KW Anderson,T Ikawa,RE Tundel,SL Buchwald,

For similar abstracts research abstracts see: abstracts research

PUBMED ID PMID:

MEDLINE DATE:

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

PUBLICATION TYPE: Research Support, Non-U.S. Gov

Journal: Journal of the American Chemical Society

VOLUME: 128

Page Numbers: 10694-5

Journal Abbreviation:

ISSN: 0002-7863

DAY: 23

MONTH: Aug

YEAR: 2006

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

Number of References:

LANGUAGE: eng

NlmUniqueID: 7503056

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

KEYWORDS:

MESH TERMS:

Chemical & Substance for Abstract: The selective reaction of aryl halides with KOH: synthesis of phenols, aromatic ethers, and benzofurans. Information

Substance Name:

Registry Number:

Grant and Affiliation Information for The selective reaction of aryl halides with KOH: synthesis of phenols, aromatic ethers, and benzofurans.

AFFILIATION: Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.

Country: United States

AGENCY:

GRANT:

ACRONYM:

MEDLINETA: J Am Chem Soc

REFSOURCE:

DATABASENAME:

ACCESSION NUMBER:

Number Hits: 0

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

• 4,7-Dimethoxy-1,10-phenanthroline: an excellent ligand for the Cu-catalyzed N-arylation of imidazoles.
• A case control study of premorbid and currently reported physical activity levels in chronic fatigue syndrome.
• A highly active catalyst for Suzuki-Miyaura cross-coupling reactions of heteroaryl compounds.
• A twin study of cognitive function in chronic fatigue syndrome: the effects of sudden illness onset.
• Benchtop monitoring of reaction progress via visual recognition with a handheld UV lamp: in situ monitoring of boronic acids in the Suzuki-Miyaura reaction.
• Cold pressor pain sensitivity in monozygotic twins discordant for chronic fatigue syndrome.
• Convenient method for the preparation of Weinreb amides via Pd-catalyzed aminocarbonylation of aryl bromides at atmospheric pressure.
• Copper-catalyzed N-arylation of imidazoles and benzimidazoles.
• Copper-catalyzed vinylation of hydrazides. A regioselective entry to highly substituted pyrroles.
• Cu-catalyzed N- and O-arylation of 2-, 3-, and 4-hydroxypyridines and hydroxyquinolines.
• Cu-catalyzed tandem C-N bond formation for the synthesis of pyrroles and heteroarylpyrroles.
• Domino cu-catalyzed C--N coupling/hydroamidation: a highly efficient synthesis of nitrogen heterocycles.
• Electronic effects on the selectivity of pd-catalyzed C-N bond-forming reactions using biarylphosphine ligands: the competitive roles of amine binding and acidity.
• Feeling bad in more ways than one: comorbidity patterns of medically unexplained and psychiatric conditions.
• Highly efficient monophosphine-based catalyst for the palladium-catalyzed suzuki-miyaura reaction of heteroaryl halides and heteroaryl boronic acids and esters.
• Highly selective room-temperature copper-catalyzed C-N coupling reactions.
• Monodentate phosphines provide highly active catalysts for Pd-catalyzed C-N bond-forming reactions of heteroaromatic halides/amines and (H)N-heterocycles.
• Mortality in a cohort of chronically fatigued patients.
• N- versus O-arylation of aminoalcohols: orthogonal selectivity in copper-based catalysts.
• Palladium-catalyzed borylation of aryl chlorides: scope, applications, and computational studies.
• Palladium-catalyzed silylation of aryl chlorides with hexamethyldisilane.
• Pd-catalyzed Kumada-Corriu cross-coupling reactions at low temperatures allow the use of Knochel-type Grignard reagents.
• Perceived discrimination in health care among American Indians/Alaska natives.
• Rationale behind the resistance of dialkylbiaryl phosphines toward oxidation by molecular oxygen.
• Selective palladium-catalyzed arylation of ammonia: synthesis of anilines as well as symmetrical and unsymmetrical di- and triarylamines.
• Significantly improved method for the pd-catalyzed coupling of phenols with aryl halides: understanding ligand effects.
• The Tlx-2 homeobox gene is a downstream target of BMP signalling and is required for mouse mesoderm development.
• The impact of a 4-hour sleep delay on slow wave activity in twins discordant for chronic fatigue syndrome.
• The influence of community-based participatory research principles on the likelihood of participation in health research in American Indian communities.
• The selective reaction of aryl halides with KOH: synthesis of phenols, aromatic ethers, and benzofurans.