Journal
ORGANIC LETTERS
Volume 10, Issue 5, Pages 1033-1035Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol800159w
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Funding
- NIGMS NIH HHS [R01 GM069445, R01 GM069445-04, R01-GM69445] Funding Source: Medline
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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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