Iridium-catalyzed C-C coupling via transfer hydrogenation: Carbonyl addition from the alcohol or aldehyde oxidation level employing 1,3-cyclohexadiene

John F. Bower; Ryan L. Patman; Michael J. Krische

doi:10.1021/ol800159w

Iridium-catalyzed C-C coupling via transfer hydrogenation: Carbonyl addition from the alcohol or aldehyde oxidation level employing 1,3-cyclohexadiene

John F. Bower, Ryan L. Patman, Michael J. Krische

School of Chemistry

Research output: Contribution to journal › Article (Academic Journal) › peer-review

101 Citations (Scopus)

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).

Original language	English
Pages (from-to)	1033-1035
Number of pages	3
Journal	Organic Letters
Volume	10
Issue number	5
DOIs	https://doi.org/10.1021/ol800159w
Publication status	Published - 6 Mar 2008

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title = "Iridium-catalyzed C-C coupling via transfer hydrogenation: Carbonyl addition from the alcohol or aldehyde oxidation level employing 1,3-cyclohexadiene",

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).",

author = "Bower, {John F.} and Patman, {Ryan L.} and Krische, {Michael J.}",

year = "2008",

month = mar,

day = "6",

doi = "10.1021/ol800159w",

language = "English",

volume = "10",

pages = "1033--1035",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "5",

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TY - JOUR

T1 - Iridium-catalyzed C-C coupling via transfer hydrogenation: Carbonyl addition from the alcohol or aldehyde oxidation level employing 1,3-cyclohexadiene

AU - Bower, John F.

AU - Patman, Ryan L.

AU - Krische, Michael J.

PY - 2008/3/6

Y1 - 2008/3/6

N2 - 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).

AB - 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).

U2 - 10.1021/ol800159w

DO - 10.1021/ol800159w

M3 - Article (Academic Journal)

C2 - 18254642

SN - 1523-7060

VL - 10

SP - 1033

EP - 1035

JO - Organic Letters

JF - Organic Letters

IS - 5

ER -

Iridium-catalyzed C-C coupling via transfer hydrogenation: Carbonyl addition from the alcohol or aldehyde oxidation level employing 1,3-cyclohexadiene

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