Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 130, Issue 20, Pages 6338-+Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja801213x
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- NIGMS NIH HHS [R01-GM069445, R01 GM069445, R01 GM069445-01A2] Funding Source: Medline
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Under the conditions of ruthenium-catalyzed transfer hydrogenation, commercially available acyclic 1,3dienes, butadiene, isoprene, and 2,3-dimethylbutadiene, couple to benzylic alcohols la -6a to furnish products of carbonyl crotylation 1b -6b, carbonyl isoprenylation 1c-6c, and carbonyl reverse 2-methyl prenylation 1d-6d. Under related transfer hydrogenation conditions employing isopropanol as terminal reductant, isoprene couples to aldehydes 7a-9a to furnish identical products of carbonyl isoprenylation 1c-3c. Thus, carbonyl allylation is achieved from the alcohol or the aldehyde oxidation level in the absence of preformed allyl metal reagents. Coupling to aliphatic alcohols (isoprene to 1-nonanol, 65% isolated yield) and allylic alcohols (isoprene to geraniol, 75% isolated yield) also is demonstrated. Isotopic labeling studies corroborate a mechanism involving hydrogen donation from the reactant alcohol or sacrificial alcohol (i-PrOH).
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