Organic Letters, volume 10, issue 5, pages 1033-1035
Iridium-Catalyzed C−C Coupling via Transfer Hydrogenation: Carbonyl Addition from the Alcohol or Aldehyde Oxidation Level Employing 1,3-Cyclohexadiene
Publication type: Journal Article
Publication date: 2008-02-07
Journal:
Organic Letters
Q1
Q1
SJR: 1.245
CiteScore: 9.3
Impact factor: 4.9
ISSN: 15237060, 15237052
PubMed ID:
18254642
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
Under hydrogen autotransfer conditions employing a catalyst derived from [Ir(cod)Cl]2 and BIPHEP, 1,3-cyclohexadiene (CHD) couples to benzylic alcohols 1a-9a to furnish carbonyl addition products 1c-9c, which appear as single diastereomers with variable quantities of regioisomeric adducts 1d-9d. Under related transfer hydrogenation conditions employing isopropanol as terminal reductant, identical carbonyl adducts 1c-9c are obtained from the aldehyde oxidation level. Isotopic labeling studies corroborate a mechanism involving hydrogen donation from the reactant alcohol or sacrificial alcohol (i-PrOH).
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Bower J. E., Patman R. L., Krische M. J. Iridium-Catalyzed C−C Coupling via Transfer Hydrogenation: Carbonyl Addition from the Alcohol or Aldehyde Oxidation Level Employing 1,3-Cyclohexadiene // Organic Letters. 2008. Vol. 10. No. 5. pp. 1033-1035.
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Bower J. E., Patman R. L., Krische M. J. Iridium-Catalyzed C−C Coupling via Transfer Hydrogenation: Carbonyl Addition from the Alcohol or Aldehyde Oxidation Level Employing 1,3-Cyclohexadiene // Organic Letters. 2008. Vol. 10. No. 5. pp. 1033-1035.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/ol800159w
UR - https://doi.org/10.1021/ol800159w
TI - Iridium-Catalyzed C−C Coupling via Transfer Hydrogenation: Carbonyl Addition from the Alcohol or Aldehyde Oxidation Level Employing 1,3-Cyclohexadiene
T2 - Organic Letters
AU - Bower, John Eric
AU - Patman, Ryan L
AU - Krische, Michael J
PY - 2008
DA - 2008/02/07
PB - American Chemical Society (ACS)
SP - 1033-1035
IS - 5
VL - 10
PMID - 18254642
SN - 1523-7060
SN - 1523-7052
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2008_Bower,
author = {John Eric Bower and Ryan L Patman and Michael J Krische},
title = {Iridium-Catalyzed C−C Coupling via Transfer Hydrogenation: Carbonyl Addition from the Alcohol or Aldehyde Oxidation Level Employing 1,3-Cyclohexadiene},
journal = {Organic Letters},
year = {2008},
volume = {10},
publisher = {American Chemical Society (ACS)},
month = {feb},
url = {https://doi.org/10.1021/ol800159w},
number = {5},
pages = {1033--1035},
doi = {10.1021/ol800159w}
}
Cite this
MLA
Copy
Bower, John Eric, et al. “Iridium-Catalyzed C−C Coupling via Transfer Hydrogenation: Carbonyl Addition from the Alcohol or Aldehyde Oxidation Level Employing 1,3-Cyclohexadiene.” Organic Letters, vol. 10, no. 5, Feb. 2008, pp. 1033-1035. https://doi.org/10.1021/ol800159w.