Journal of the American Chemical Society, volume 131, issue 6, pages 2066-2067
Direct Vinylation of Alcohols or Aldehydes Employing Alkynes as Vinyl Donors: A Ruthenium Catalyzed C−C Bond-Forming Transfer Hydrogenation
Publication type: Journal Article
Publication date: 2009-01-27
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 15
ISSN: 00027863, 15205126
General Chemistry
Catalysis
Biochemistry
Colloid and Surface Chemistry
Abstract
Under the conditions of ruthenium catalyzed transfer hydrogenation, 2-butyne couples to benzylic and aliphatic alcohols 1a-1l to furnish allylic alcohols 2a-2l, constituting a direct C-H vinylation of alcohols employing alkynes as vinyl donors. Under related transfer hydrogenation conditions employing formic acid as terminal reductant, 2-butyne couples to aldehydes 4a, 4b, and 4e to furnish identical products of carbonyl vinylation 2a, 2b, and 2e. Thus, carbonyl vinylation is achieved from the alcohol or the aldehyde oxidation level in the absence of any stoichiometric metallic reagents. Nonsymmetric alkynes 6a-6c couple efficiently to aldehyde 4b to provide allylic alcohols 2m-2o as single regioisomers. Acetylenic aldehyde 7a engages in efficient intramolecular coupling to deliver cyclic allylic alcohol 8a.
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Citations by publishers
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Wiley
47 publications, 37.3%
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American Chemical Society (ACS)
47 publications, 37.3%
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1 publication, 0.79%
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Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii
1 publication, 0.79%
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- We do not take into account publications without a DOI.
- Statistics recalculated only for publications connected to researchers, organizations and labs registered on the platform.
- Statistics recalculated weekly.
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Patman R. L. et al. Direct Vinylation of Alcohols or Aldehydes Employing Alkynes as Vinyl Donors: A Ruthenium Catalyzed C−C Bond-Forming Transfer Hydrogenation // Journal of the American Chemical Society. 2009. Vol. 131. No. 6. pp. 2066-2067.
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Patman R. L., Chaulagain M. R., Williams V. M., Krische M. J. Direct Vinylation of Alcohols or Aldehydes Employing Alkynes as Vinyl Donors: A Ruthenium Catalyzed C−C Bond-Forming Transfer Hydrogenation // Journal of the American Chemical Society. 2009. Vol. 131. No. 6. pp. 2066-2067.
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TY - JOUR
DO - 10.1021/ja809456u
UR - https://doi.org/10.1021/ja809456u
TI - Direct Vinylation of Alcohols or Aldehydes Employing Alkynes as Vinyl Donors: A Ruthenium Catalyzed C−C Bond-Forming Transfer Hydrogenation
T2 - Journal of the American Chemical Society
AU - Chaulagain, Mani Raj
AU - Williams, Vanessa M
AU - Patman, Ryan L
AU - Krische, Michael J
PY - 2009
DA - 2009/01/27 00:00:00
PB - American Chemical Society (ACS)
SP - 2066-2067
IS - 6
VL - 131
SN - 0002-7863
SN - 1520-5126
ER -
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@article{2009_Patman,
author = {Mani Raj Chaulagain and Vanessa M Williams and Ryan L Patman and Michael J Krische},
title = {Direct Vinylation of Alcohols or Aldehydes Employing Alkynes as Vinyl Donors: A Ruthenium Catalyzed C−C Bond-Forming Transfer Hydrogenation},
journal = {Journal of the American Chemical Society},
year = {2009},
volume = {131},
publisher = {American Chemical Society (ACS)},
month = {jan},
url = {https://doi.org/10.1021/ja809456u},
number = {6},
pages = {2066--2067},
doi = {10.1021/ja809456u}
}
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MLA
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Patman, Ryan L., et al. “Direct Vinylation of Alcohols or Aldehydes Employing Alkynes as Vinyl Donors: A Ruthenium Catalyzed C−C Bond-Forming Transfer Hydrogenation.” Journal of the American Chemical Society, vol. 131, no. 6, Jan. 2009, pp. 2066-2067. https://doi.org/10.1021/ja809456u.