Journal
NATURE COMMUNICATIONS
Volume 12, Issue 1, Pages -Publisher
NATURE RESEARCH
DOI: 10.1038/s41467-021-23058-3
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Funding
- National Key Research and Development Program of China [2016YFB0101203]
- Wuhan University
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The derivatives of heterocycles 2-pyridone and uracil are important pharmacophores in medicinal chemistry, and there is an urgent need for diverse synthesis of such derivatives. This study demonstrates that palladium/norbornene cooperative catalysis enables dual-functionalization of iodinated 2-pyridones and uracils.
Heterocycles 2-pyridone and uracil are privileged pharmacophores. Diversity-oriented synthesis of their derivatives is in urgent need in medicinal chemistry. Herein, we report a palladium/norbornene cooperative catalysis enabled dual-functionalization of iodinated 2-pyridones and uracils. The success of this research depends on the use of two unique norbornene derivatives as the mediator. Readily available alkyl halides/tosylates and aryl bromides are utilized as ortho-alkylating and -arylating reagents, respectively. Widely accessible ipso-terminating reagents, including H/DCO2Na, boronic acid/ester, terminal alkene and alkyne are compatible with this protocol. Thus, a large number of valuable 2-pyridone derivatives, including deuterium/CD3-labeled 2-pyridones, bicyclic 2-pyridones, 2-pyridone-fenofibrate conjugate, axially chiral 2-pyridone (97% ee), as well as uracil and thymine derivatives, can be quickly prepared in a predictable manner (79 examples reported), which will be very useful in new drug discovery. Diversity-oriented synthesis of 2-pyridone and uracil derivatives is in urgent need in medicinal chemistry as they are useful pharmacophores. Here the authors show that palladium/norbornene cooperative catalysis enabled dual-functionalization of iodinated 2- pyridones and uracils.
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