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

被引：102

作者：

Bower, John F. ^{[1
]}

Patman, Ryan L. ^{[1
]}

Krische, Michael J. ^{[1
]}

机构：

[1] Univ Texas Austin, Dept Chem & Biochem, Austin, TX 78712 USA

来源：

ORGANIC LETTERS | 2008年 / 10卷 / 05期

关键词：

D O I：

10.1021/ol800159w

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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).

引用

页码：1033 / 1035

页数：3

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