Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 141, Issue 30, Pages 11806-11810Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.9b05604
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Funding
- Office of Science, Office of Basic Energy Sciences
- Division of Chemical Sciences, Geosciences, and Bioscience of the U.S. Department of Energy at Lawrence Berkeley National Laboratory [DE-AC02-05CH11231]
- NIH Postdoctoral Fellowship [1F32GM129933-01]
- NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES [F32GM129933] Funding Source: NIH RePORTER
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Performing selective transformations on complex substrates remains a challenge in synthetic chemistry. These difficulties often arise due to cross-reactivity, particularly in the presence of similar functional groups at multiple sites. Therefore, there is a premium on the ability to perform selective activation of these functional groups. We report here a supramolecular strategy where encapsulation of a hydrogenation catalyst enables selective olefin hydrogenation, even in the presence of multiple sites of unsaturation. While the reaction requires at least one sterically nondemanding alkene substituent, the rate of hydrogenation is not sensitive to the distance between the alkene and the functional group, including a carboxylate, on the other substituent. This observation indicates that only the double bond has to be encapsulated to effect hydrogenation. Going further, we demonstrate that this supramolecular strategy can overcome the inherent allylic alcohol selectivity of the free catalyst, achieving supra molecular catalyst-directed regioselectivity as opposed to directing-group selectivity.
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