Journal
ORGANIC LETTERS
Volume 21, Issue 21, Pages 8837-8841Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b03475
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Funding
- Research Grant of Institute of Natural Sciences at Nihon University
- Japan Society for the Promotion of Science [17K05794]
- Grants-in-Aid for Scientific Research [17K05794] Funding Source: KAKEN
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The nickel-catalyzed benzylic substitution of benzyl alcohol derivatives with a soft carbon nucleophile is extremely rare compared to that with a hard carbon nucleophile. We have achieved the nickel-catalyzed benzylic substitution of benzyl esters with malonates as a soft carbon nucleophile. Primary and secondary benzyl 2,3,4,5,6-penta-fluorobenzoates as well as a wide variety of malonate derivatives were well tolerated in the nickel-catalyzed reaction, providing the corresponding alkylation products in 46-86% yields (34 examples). Additionally, we propose a possible reaction mechanism that would undergo via the eta(1)- and eta(3)-benzylnickel intermediates.
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