Mild iridium-catalyzed borylation of arenes. High turnover numbers, room temperature reactions, and isolation of a potential intermediate.

Mild iridium-catalyzed borylation of arenes. High turnover numbers, room temperature reactions, and isolation of a potential intermediate. Research Abstract Details 

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Mild iridium-catalyzed borylation of arenes. High turnover numbers, room temperature reactions, and isolation of a potential intermediate. Abstract Text:

Tatsuo Ishiyama,Jun Takagi,Kousaku Ishida,Norio Miyaura,Natia R Anastasi,John F Hartwig,

The borylation of arenes leads to the formation of synthetically versatile products from unactivated arene reagents. We report that Ir(I) precursors in conjunction with bipyridine ligands catalyze in high yields the borylation of arenes under mild conditions. These reactions encompase arenes bearing both electron-withdrawing and electron-donating substituents. The temperatures required for the transformation are much lower than those previously reported for direct arene borylation. The combination of [Ir(COE)2Cl]2 and (4,4-di-t-butyl)bipyridine even allows for reaction at room temperature. The same catalyst system at 100 degrees C provides remarkably high turnover numbers for a hydrocarbon functionalization process. Mechanistic studies show that the reactions involve uncommon, Ir(II) tris-boryl complexes. An example of this type of complex ligated by di-t-butylbipyridine was isolated and structurally characterized. It reacted rapidly at room temperature to produce aryl boronate esters in high yields.

Mild iridium-catalyzed borylation of arenes. High turnover numbers, room temperature reactions, and isolation of a potential intermediate. Publishing Authors By Initials

T Ishiyama,J Takagi,K Ishida,N Miyaura,NR Anastasi,JF Hartwig,

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Mild iridium-catalyzed borylation of arenes. High turnover numbers, room temperature reactions, and isolation of a potential intermediate. Journal Published:

PUBLICATION TYPE: Journal Article

Journal: Journal of the American Chemical Society

VOLUME: 124

Page Numbers: 390-1

Journal Abbreviation: J. Am. Chem. Soc.

ISSN: 0002-7863

DAY: 23

MONTH: Jan

YEAR: 2002

Mild iridium-catalyzed borylation of arenes. High turnover numbers, room temperature reactions, and isolation of a potential intermediate. Information

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LANGUAGE: eng

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Grant and Affiliation Information for Mild iridium-catalyzed borylation of arenes. High turnover numbers, room temperature reactions, and isolation of a potential intermediate.

AFFILIATION: Department of Chemistry, Yale University, P.O. Box 208107, New Haven, Connecticut 06520-8107, USA.

Country: United States

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MEDLINETA: J Am Chem Soc

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