Journal
ASIAN JOURNAL OF ORGANIC CHEMISTRY
Volume 5, Issue 8, Pages 971-975Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ajoc.201600235
Keywords
arylation; borylation; Heck reaction; oxindoles; palladium
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Funding
- Natural Science Foundation of China [21572118, 21372144, JQ201505]
- Natural Science Foundation of Shandong province [21572118, 21372144, JQ201505]
- fundamental Research&Subject construction funds of Shandong University [2014JC008, 104.205.2.5]
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3,3-Disubstituted oxindole derivatives are privileged five-membered heterocycles widely presented in a variety of natural products and pharmaceuticals with significant biological activities. In this paper, diverse boron-substituted oxindoles have been successfully synthesized by Pd-catalyzed intramolecular arylation and borylation cascade of unsaturated amides. More importantly, simply switching the reaction solvents led to other reductive Heck products with the same catalyst and reactants. Control experiments showed that the reductive Heck products were transformed from 3,3-disubstituted oxindole boronic esters in the presence of base.
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