Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 17, Issue 44, Pages 12437-12443Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201101554
Keywords
green chemistry; homogeneous catalysis; hydrogenation; ruthenium; transfer hydrogenation; vinylation
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Funding
- NIGMS NIH HHS [R01 GM069445-05, R01-GM069445, R01 GM069445] Funding Source: Medline
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Nonsymmetric 1,2-disubstituted alkynes engage in reductive coupling to a variety of aldehydes under the conditions of ruthenium-catalyzed transfer hydrogenation by employing formic acid as the terminal reductant and delivering the products of carbonyl vinylation with good to excellent levels of regioselectivity and with complete control of olefin stereochemistry. As revealed in an assessment of the ruthenium counterion, iodide plays an essential role in directing the regioselectivity of C-C bond formation. Isotopic labeling studies corroborate reversible catalytic propargyl C-H oxidative addition in advance of the C-C coupling, and demonstrate that the C-C coupling products do not experience reversible dehydrogenation by way of enone intermediates. This transfer hydrogenation protocol enables carbonyl vinylation in the absence of stoichiometric metallic reagents.
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