Dehydrogenation of Inert Alkyl Groups via Remote C−H Activation: Converting a Propyl Group into a π-Allylic Complex

Ramesh GIRI; Nathan MAUGEL; Bruce M FOXMAN; Jin-Quan YU

doi:10.1021/om8000444

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Dehydrogenation of Inert Alkyl Groups via Remote C−H Activation: Converting a Propyl Group into a π-Allylic Complex

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Dehydrogenation of Inert Alkyl Groups via Remote C−H Activation: Converting a Propyl Group into a π-Allylic Complex

Ramesh GIRI, Nathan MAUGEL, Bruce M FOXMAN and Jin-Quan YU

Organometallics, Vol.27(8), pp.1667-1670

04/01/2008

DOI: https://doi.org/10.1021/om8000444

Abstract

Palladium

Organic compounds

Anions

Ethyl groups

Organic reactions

Pd(OAc)2-mediated dehydrogenation of an alkyl group to a double bond or a η3-allylic complex via sp3 C−H bond activation and allylic oxidation is reported. A novel redox is proposed for this double oxidation under oxidant-free conditions. A catalytic protocol using benzoquinone as the stoichiometric oxidant has also been developed for the dehydrogenation of cyclopentylcarboxamides.

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Title: Dehydrogenation of Inert Alkyl Groups via Remote C−H Activation: Converting a Propyl Group into a π-Allylic Complex
Creators: Ramesh GIRI - Department of Chemistry, The Scripps Research Institute, La Jolla, California 92037, and Department of Chemistry MS015, Brandeis University, Waltham, Massachusetts 02454
Nathan MAUGEL - Department of Chemistry, The Scripps Research Institute, La Jolla, California 92037, and Department of Chemistry MS015, Brandeis University, Waltham, Massachusetts 02454
Bruce M FOXMAN - Department of Chemistry, The Scripps Research Institute, La Jolla, California 92037, and Department of Chemistry MS015, Brandeis University, Waltham, Massachusetts 02454
Jin-Quan YU - Department of Chemistry, The Scripps Research Institute, La Jolla, California 92037, and Department of Chemistry MS015, Brandeis University, Waltham, Massachusetts 02454
Publication Details: Organometallics, Vol.27(8), pp.1667-1670
Publisher: American Chemical Society
Identifiers: 9923989568301921
Academic Unit: Department of Chemistry
Language: English
Resource Type: Journal article

Dehydrogenation of Inert Alkyl Groups via Remote C−H Activation: Converting a Propyl Group into a π-Allylic Complex

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