Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 144, Issue 11, Pages 4810-4818Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.2c00962
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Funding
- National Key R&D Program of China [2021YFA1500200]
- National Natural Science Foundation of China [21871147, 91956106]
- Natural Science Foundation of Tianjin [20JCZDJC00720, 20JCJQJC00030]
- Fundamental Research Funds for Central Universities [2122018165]
- Haihe Laboratory of Sustainable Chemical Transformations, Frontiers Science Center for New Organic Matter at Nankai University [63181206]
- Tencent Foundation
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This study reports a borane-catalyzed tandem reaction method that achieves exclusively C3-selective alkylation of pyridines, providing a practical tool for late-stage functionalization of structurally complex pharmaceuticals bearing a pyridine moiety.
Achieving C3-selective pyridine functionalization isa longstanding challenge in organic chemistry. The existingmethods, including electrophilic aromatic substitution and C-Hactivation, often require harsh reaction conditions and excesspyridine and generate multiple regioisomers. Herein, we report amethod for borane-catalyzed tandem reactions that result inexclusively C3-selective alkylation of pyridines. These tandemreactions consist of pyridine hydroboration, nucleophilic additionof the resulting dihydropyridine to an imine, an aldehyde, or a ketone, and subsequent oxidative aromatization. Because the pyridineis the limiting reactant and the reaction conditions are mild, this method constitutes a practical tool for late-stage functionalization ofstructurally complex pharmaceuticals bearing a pyridine moiety.
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