Borrowing hydrogen: Indirect "Wittig" olerination for the formation of C-C bonds from alcohols

P J Black, M G Edwards, J M J Williams

Research output: Contribution to journalArticle

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Abstract

The successful development of an indirect three-step domino sequence for the formation of C-C bonds from alcohol substrates is described. An iridium-catalysed dehydrogenation of alcohol I affords the intermediate aldehyde 2. The desired C-C bond can then be formed by a facile Wittig olefination, yielding the intermediate alkene 3. In the final step the alkene is hydrogenated to afford the indirect Wittig product, the alkane 4. The key to this process is the concept of borrowing hydrogen; hydrogen removed in the initial dehydrogenation step is simply borrowed by the iridium catalyst. Functioning as a hydrogen reservoir, the catalyst facilitates C-C bond formation before subsequently returning the borrowed hydrogen in the final step. Herein we present full details of our examination into both the substrate and reaction scope and the limitations of the catalytic cycle. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006).
Original languageEnglish
Pages (from-to)4367-4378
Number of pages12
JournalEuropean Journal of Organic Chemistry
Issue number19
DOIs
Publication statusPublished - 2006

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Hydrogen
alcohols
Alcohols
Iridium
Alkenes
hydrogen
Dehydrogenation
dehydrogenation
iridium
alkenes
catalysts
Catalysts
Alkanes
Substrates
Germany
aldehydes
Aldehydes
alkanes
examination
cycles

Cite this

Borrowing hydrogen: Indirect "Wittig" olerination for the formation of C-C bonds from alcohols. / Black, P J; Edwards, M G; Williams, J M J.

In: European Journal of Organic Chemistry, No. 19, 2006, p. 4367-4378.

Research output: Contribution to journalArticle

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