Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 139, Issue 10, Pages 3904-3910Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.7b00823
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Funding
- National Natural Science Foundation of China [21333004, 21361140376, 21572099, 21332005]
- Qing Lan Project
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Density functional theory investigations revealed that the pyridine-boryl radical generated in situ using 4-cyanopyridine and bis(pinacolato)diboron could be used as a bifunctional reagent, which serves as not only a pyridine precursor but also a boryl radical. With the unique reactivity of I such radicals, 4-substituted pyridine derivatives could be synthesized using alpha,beta-unsaturated ketones and 4-cyanopyridine via a novel radical addition/C-C coupling mechanism. Several controlled experiments were conducted to provide supportive evidence for the proposed mechanism. In addition to enones, the scope could be extended to a wide range of boryl radical acceptors, including various aldehydes and ketones, aryl imines and alkynones. Lastly, this transformation was applied in the late-stage modification of a complicated pharmaceutical molecule.
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