Regiospecific functionalization of methyl C-H bonds of alkyl groups in reagents with heteroatom functionality.

Regiospecific functionalization of methyl C-H bonds of alkyl groups in reagents with heteroatom functionality. Research Abstract Details 

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Regiospecific functionalization of methyl C-H bonds of alkyl groups in reagents with heteroatom functionality. Abstract Text:

Joshua D Lawrence,Makoto Takahashi,Chulsung Bae,John F Hartwig,

We report the regiospecific, rhodium-catalyzed borylation of saturated terminal C-H bonds in molecules with existing functionality. Moderate to good yields were obtained with the organic substrate in excess and as limiting reagent. The borylations of trialkylamines, protected alcohols, protected ketones, and fluoroalkanes occurred regiospecifically at the methyl group that is least sterically hindered. Reactions were also conducted that probed electronic effects on the alkyl borylation. These reactions showed that the borylation occurred preferentially at the methyl group that is most electron-deficient. Methods to conduct tandem borylation of C-H bonds and conversion of the resulting boronate esters to alcohols, alkylarenes, and alkyltrifluoroborates were also developed.

Regiospecific functionalization of methyl C-H bonds of alkyl groups in reagents with heteroatom functionality. Publishing Authors By Initials

JD Lawrence,M Takahashi,C Bae,JF Hartwig,

For similar organic chemicals: ethers research abstracts see: organic chemicals: ethers research

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Regiospecific functionalization of methyl C-H bonds of alkyl groups in reagents with heteroatom functionality. Journal Published:

PUBLICATION TYPE: Research Support, U.S. Gov't,

Journal: Journal of the American Chemical Society

VOLUME: 126

Page Numbers: 15334-5

Journal Abbreviation: J. Am. Chem. Soc.

ISSN: 0002-7863

DAY: 1

MONTH: Dec

YEAR: 2004

Regiospecific functionalization of methyl C-H bonds of alkyl groups in reagents with heteroatom functionality. Information

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LANGUAGE: eng

NlmUniqueID: 7503056

Regiospecific functionalization of methyl C-H bonds of alkyl groups in reagents with heteroatom functionality. Keywords Mesh Terms:

KEYWORDS: Ethers

MESH TERMS: chemistry

Chemical & Substance for Abstract: Regiospecific functionalization of methyl C-H bonds of alkyl groups in reagents with heteroatom functionality. Information

Substance Name: bis(pinacolato)diboron

Registry Number: 0

Grant and Affiliation Information for Regiospecific functionalization of methyl C-H bonds of alkyl groups in reagents with heteroatom functionality.

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

Country: United States

AGENCY: United States NIGMS

GRANT: GM 069172

ACRONYM: GM

MEDLINETA: J Am Chem Soc

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