化学
硼氢化
对映选择合成
吡啶
硼烷
铱
芳构化
组合化学
催化作用
亲核细胞
分子内力
表面改性
硼烷
有机化学
硼
物理化学
作者
Zhong Liu,Zhu-Jun Shi,Lu Liu,Ming Zhang,Mengchen Zhang,Hai‐Ming Guo,Xiao‐Chen Wang
摘要
Asymmetric intermolecular C–H functionalization of pyridines at C3 is unprecedented. Herein, we report the first examples of such transformations: specifically, C3-allylation of pyridines via tandem borane and iridium catalysis. First, borane-catalyzed pyridine hydroboration generates nucleophilic dihydropyridines; then, the dihydropyridine undergoes enantioselective iridium-catalyzed allylation; and finally, oxidative aromatization with air as the oxidant gives the C3-allylated pyridine. This protocol provides direct access to C3-allylated pyridines with excellent enantioselectivity (up to >99% ee) and is suitable for late-stage functionalization of pyridine-containing drugs.
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