Journal of the American Chemical Society, volume 129, issue 49, pages 15134-15135
Catalytic C−C Coupling via Transfer Hydrogenation: Reverse Prenylation, Crotylation, and Allylation from the Alcohol or Aldehyde Oxidation Level
Publication type: Journal Article
Publication date: 2007-11-17
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 15
ISSN: 00027863, 15205126
General Chemistry
Catalysis
Biochemistry
Colloid and Surface Chemistry
Abstract
We report byproduct-free carbonyl reverse prenylation, crotylation, and allylation from the alcohol oxidation state via alcohol−allene hydrogen autotransfer. Specifically, exposure of alcohols 1a−6a to 1,1-dimethylallene, methylallene, and allene in the presence of [Ir(cod)(BIPHEP)]BARF (5−7.5 mol %) delivers reverse prenylation products 1c−6c, crotylation products 1d−3d, and allylation product 1e. Similarly, under the conditions of transfer hydrogenation employing isopropanol as terminal reductant, aldehydes 1b−6b are converted to the very same adducts 1c−6c, 1d−3d, and 1e. Isotopic labeling studies corroborate a mechanism involving hydrogen donation from the reactant alcohol or sacrificial alcohol (i-PrOH). The ability to achieve carbonyl addition directly from the alcohol oxidation level circumvents the redox manipulations so often required to convert alcohols to aldehydes. Further, through hydrogen autotransfer, there resides the potential to develop myriad byproduct-free carbonyl additions wherein al...
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1 publication, 0.67%
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1 publication, 0.67%
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Citations by publishers
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60
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American Chemical Society (ACS)
60 publications, 40.27%
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Wiley
49 publications, 32.89%
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16 publications, 10.74%
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10 publications, 6.71%
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Springer Nature
5 publications, 3.36%
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4 publications, 2.68%
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The Chemical Society of Japan
1 publication, 0.67%
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1 publication, 0.67%
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1 publication, 0.67%
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Walter de Gruyter
1 publication, 0.67%
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Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii
1 publication, 0.67%
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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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Bower J. E. et al. Catalytic C−C Coupling via Transfer Hydrogenation: Reverse Prenylation, Crotylation, and Allylation from the Alcohol or Aldehyde Oxidation Level // Journal of the American Chemical Society. 2007. Vol. 129. No. 49. pp. 15134-15135.
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Bower J. E., Skucas E., Patman R. L., Krische M. J. Catalytic C−C Coupling via Transfer Hydrogenation: Reverse Prenylation, Crotylation, and Allylation from the Alcohol or Aldehyde Oxidation Level // Journal of the American Chemical Society. 2007. Vol. 129. No. 49. pp. 15134-15135.
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TY - JOUR
DO - 10.1021/ja077389b
UR - https://doi.org/10.1021/ja077389b
TI - Catalytic C−C Coupling via Transfer Hydrogenation: Reverse Prenylation, Crotylation, and Allylation from the Alcohol or Aldehyde Oxidation Level
T2 - Journal of the American Chemical Society
AU - Skucas, Eduardas
AU - Bower, John Eric
AU - Patman, Ryan L
AU - Krische, Michael J
PY - 2007
DA - 2007/11/17 00:00:00
PB - American Chemical Society (ACS)
SP - 15134-15135
IS - 49
VL - 129
SN - 0002-7863
SN - 1520-5126
ER -
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@article{2007_Bower,
author = {Eduardas Skucas and John Eric Bower and Ryan L Patman and Michael J Krische},
title = {Catalytic C−C Coupling via Transfer Hydrogenation: Reverse Prenylation, Crotylation, and Allylation from the Alcohol or Aldehyde Oxidation Level},
journal = {Journal of the American Chemical Society},
year = {2007},
volume = {129},
publisher = {American Chemical Society (ACS)},
month = {nov},
url = {https://doi.org/10.1021/ja077389b},
number = {49},
pages = {15134--15135},
doi = {10.1021/ja077389b}
}
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MLA
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Bower, John Eric, et al. “Catalytic C−C Coupling via Transfer Hydrogenation: Reverse Prenylation, Crotylation, and Allylation from the Alcohol or Aldehyde Oxidation Level.” Journal of the American Chemical Society, vol. 129, no. 49, Nov. 2007, pp. 15134-15135. https://doi.org/10.1021/ja077389b.