Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 75, Issue 9, Pages 2981-2988Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo100256t
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Funding
- National Natural Science Foundation of China [20972154, 20572108]
- Chinese Academy of Sciences
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Although a notable feature of Noyori's Ru-TsDPEN complex is that the transfer hydrogenation reaction is highly chemoselective for the C=O functional group and tolerant of alkenes, our early report indicated that the chemoselectivity could be switched from C=O to C=C bonds in the transfer hydrogenation of activated alpha,beta-unsaturated ketones. Now we have found that a variety of alpha,beta-unsaturated ketones, even without other electron-withdrawing functional groups, could be reduced on the alkenic double bonds with high selectivities employing amido-rhodium hydride complex in aqueous media, and up to 100% chemoselectivity has been achieved. It is notable that the chemoselectivity was improved significantly on going from organic solvent to water. Moreover, a 1,4-addition mechanism has been proposed on the basis of the corresponding experimental details and computational analysis.
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