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

John Eric Bower ¹

Ryan L Patman ¹

Michael J Krische ¹

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University of Texas at Austin, Department of Chemistry and Biochemistry, Austin, Texas 78712 |

Publication type: Journal Article

Publication date: 2008-02-07

American Chemical Society (ACS)

Journal: Organic Letters

Quartile SCImago

Quartile WOS

Impact factor: 5.2

ISSN: 15237060, 15237052

DOI: 10.1021/ol800159w

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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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ACS Catalysis	ACS Catalysis, 2, 1.69% ACS Catalysis 2 publications, 1.69%
Science	Science, 2, 1.69% Science 2 publications, 1.69%
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Journal of Organic Chemistry	Journal of Organic Chemistry, 1, 0.85% Journal of Organic Chemistry 1 publication, 0.85%
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Chemical Science	Chemical Science, 1, 0.85% Chemical Science 1 publication, 0.85%
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Citations by publishers

	5 10 15 20 25 30 35 40 45
Wiley	Wiley, 44, 37.29% Wiley 44 publications, 37.29%
American Chemical Society (ACS)	American Chemical Society (ACS), 39, 33.05% American Chemical Society (ACS) 39 publications, 33.05%
Royal Society of Chemistry (RSC)	Royal Society of Chemistry (RSC), 12, 10.17% Royal Society of Chemistry (RSC) 12 publications, 10.17%
Elsevier	Elsevier, 10, 8.47% Elsevier 10 publications, 8.47%
The Chemical Society of Japan	The Chemical Society of Japan, 3, 2.54% The Chemical Society of Japan 3 publications, 2.54%
Springer Nature	Springer Nature, 3, 2.54% Springer Nature 3 publications, 2.54%
Thieme	Thieme, 2, 1.69% Thieme 2 publications, 1.69%
American Association for the Advancement of Science (AAAS)	American Association for the Advancement of Science (AAAS), 2, 1.69% American Association for the Advancement of Science (AAAS) 2 publications, 1.69%
Walter de Gruyter	Walter de Gruyter, 1, 0.85% Walter de Gruyter 1 publication, 0.85%
Proceedings of the National Academy of Sciences (PNAS)	Proceedings of the National Academy of Sciences (PNAS), 1, 0.85% Proceedings of the National Academy of Sciences (PNAS) 1 publication, 0.85%
Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii	Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii, 1, 0.85% Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii 1 publication, 0.85%
	5 10 15 20 25 30 35 40 45

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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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RIS |

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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 00:00:00

PB - American Chemical Society (ACS)

SP - 1033-1035

IS - 5

VL - 10

SN - 1523-7060

SN - 1523-7052

ER -

BibTex |

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@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}

}

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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.

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Publisher

American Chemical Society (ACS)

Journal

Organic Letters

Quartile SCImago

Quartile WOS

Impact factor

5.2

ISSN

15237060 (Print)
15237052 (Electronic)