Amine-directed hydroboration: scope and limitations.

Amine-directed hydroboration: scope and limitations. Research Abstract Details 

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Amine-directed hydroboration: scope and limitations. Abstract Text:

Iodine activation induces intramolecular hydroboration of homoallylic and bis-homoallylic amine boranes with good to excellent control of regiochemistry compared to control experiments using excess THF*BH 3. Deuterium labeling and other evidence confirm that the iodine-induced hydroboration reaction of homoallylic amine boranes occurs via an intramolecular mechanism equivalent to the classical 4-center process and without competing retro-hydroboration. Longer carbon chain tethers result in lower regioselectivity, whereas the shorter tether in allylic amines results in a switch to dominant intermolecular hydroboration. Regioselectivity in THF*BH 3 control experiments is higher for the allylic amine boranes compared to the iodine activation experiments, whereas the reverse is true for homoallylic amine borane activation.

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Amine-directed hydroboration: scope and limitations. Journal Published:

PUBLICATION TYPE: Research Support, N.I.H., Extr

Journal: Journal of the American Chemical Society

VOLUME: 130

Page Numbers: 8669-76

Journal Abbreviation: J. Am. Chem. Soc.

ISSN: 1520-5126

DAY: 13

MONTH: 06

YEAR: 2008

Amine-directed hydroboration: scope and limitations. Information

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LANGUAGE: eng

NlmUniqueID: 7503056

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Grant and Affiliation Information for Amine-directed hydroboration: scope and limitations.

AFFILIATION: Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109, USA.

Country: United States

AGENCY: United States NIGMS

GRANT: GM067146

ACRONYM: GM

MEDLINETA: J Am Chem Soc

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