Journal of the American Chemical Society, volume 130, issue 20, pages 6338-6339
Ruthenium-Catalyzed C−C Bond Forming Transfer Hydrogenation: Carbonyl Allylation from the Alcohol or Aldehyde Oxidation Level Employing Acyclic 1,3-Dienes as Surrogates to Preformed Allyl Metal Reagents
Publication type: Journal Article
Publication date: 2008-04-29
Q1
Q1
SJR: 5.489
CiteScore: 24.4
Impact factor: 14.4
ISSN: 00027863, 15205126
PubMed ID:
18444617
General Chemistry
Catalysis
Biochemistry
Colloid and Surface Chemistry
Abstract
Under the conditions of ruthenium-catalyzed transfer hydrogenation, commercially available acyclic 1,3-dienes, butadiene, isoprene, and 2,3-dimethylbutadiene, couple to benzylic alcohols 1a-6a to furnish products of carbonyl crotylation 1b-6b, carbonyl isoprenylation 1c-6c, and carbonyl reverse 2-methyl prenylation 1d-6d. Under related transfer hydrogenation conditions employing isopropanol as terminal reductant, isoprene couples to aldehydes 7a-9a to furnish identical products of carbonyl isoprenylation 1c-3c. Thus, carbonyl allylation is achieved from the alcohol or the aldehyde oxidation level in the absence of preformed allyl metal reagents. Coupling to aliphatic alcohols (isoprene to 1-nonanol, 65% isolated yield) and allylic alcohols (isoprene to geraniol, 75% isolated yield) also is demonstrated. Isotopic labeling studies corroborate a mechanism involving hydrogen donation from the reactant alcohol or sacrificial alcohol (i-PrOH).
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Shibahara F., Bower J. E., Krische M. J. Ruthenium-Catalyzed C−C Bond Forming Transfer Hydrogenation: Carbonyl Allylation from the Alcohol or Aldehyde Oxidation Level Employing Acyclic 1,3-Dienes as Surrogates to Preformed Allyl Metal Reagents // Journal of the American Chemical Society. 2008. Vol. 130. No. 20. pp. 6338-6339.
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Shibahara F., Bower J. E., Krische M. J. Ruthenium-Catalyzed C−C Bond Forming Transfer Hydrogenation: Carbonyl Allylation from the Alcohol or Aldehyde Oxidation Level Employing Acyclic 1,3-Dienes as Surrogates to Preformed Allyl Metal Reagents // Journal of the American Chemical Society. 2008. Vol. 130. No. 20. pp. 6338-6339.
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TY - JOUR
DO - 10.1021/ja801213x
UR - https://doi.org/10.1021/ja801213x
TI - Ruthenium-Catalyzed C−C Bond Forming Transfer Hydrogenation: Carbonyl Allylation from the Alcohol or Aldehyde Oxidation Level Employing Acyclic 1,3-Dienes as Surrogates to Preformed Allyl Metal Reagents
T2 - Journal of the American Chemical Society
AU - Shibahara, Fumitoshi
AU - Bower, John Eric
AU - Krische, Michael J
PY - 2008
DA - 2008/04/29
PB - American Chemical Society (ACS)
SP - 6338-6339
IS - 20
VL - 130
PMID - 18444617
SN - 0002-7863
SN - 1520-5126
ER -
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@article{2008_Shibahara,
author = {Fumitoshi Shibahara and John Eric Bower and Michael J Krische},
title = {Ruthenium-Catalyzed C−C Bond Forming Transfer Hydrogenation: Carbonyl Allylation from the Alcohol or Aldehyde Oxidation Level Employing Acyclic 1,3-Dienes as Surrogates to Preformed Allyl Metal Reagents},
journal = {Journal of the American Chemical Society},
year = {2008},
volume = {130},
publisher = {American Chemical Society (ACS)},
month = {apr},
url = {https://doi.org/10.1021/ja801213x},
number = {20},
pages = {6338--6339},
doi = {10.1021/ja801213x}
}
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Shibahara, Fumitoshi, et al. “Ruthenium-Catalyzed C−C Bond Forming Transfer Hydrogenation: Carbonyl Allylation from the Alcohol or Aldehyde Oxidation Level Employing Acyclic 1,3-Dienes as Surrogates to Preformed Allyl Metal Reagents.” Journal of the American Chemical Society, vol. 130, no. 20, Apr. 2008, pp. 6338-6339. https://doi.org/10.1021/ja801213x.