Intermolecular Aryne Ene Reaction of Hantzsch Esters: Stable Covalent Ene Adducts from a 1,4-Dihydropyridine Reaction.
Intermolecular Aryne Ene Reaction of Hantzsch Esters: Stable Covalent Ene Adducts from a 1,4-Dihydropyridine Reaction.
复制标题
DOI：
10.1021/acs.orglett.7b02272
复制
发表时间：
2017-08
期刊：
影响因子：
5.2
通讯作者：
Piera Trinchera;Weitao Sun;Jane E. Smith;D. Palomas;R. Crespo‐Otero;C. Jones
中科院分区：
文献类型：
--
作者：
Piera Trinchera;Weitao Sun;Jane E. Smith;D. Palomas;R. Crespo‐Otero;C. Jones
芳炔与1,4-二氢吡啶的反应通过区域选择性C-2或C-3芳基化得到2-芳基-1,2-二氢吡啶或2-亚甲基-3-芳基-1,2,3,4-四氢吡啶。这些化合物是二氢吡啶和不饱和底物之间形成的第一系列可分离且实验室稳定的共价烯加合物。实验研究和 DFT 计算为协同分子间芳炔过程提供了机制支持，这可能对 NAD(P)H 模型反应产生影响。
The reaction of arynes with 1,4-dihydropyridines affords 2-aryl-1,2-dihydropyridines or 2-methylene-3-aryl-1,2,3,4-tetrahydropyridines via a regioselective C-2 or C-3 arylation. These compounds are the first series of isolable and bench-stable covalent ene adducts formed between dihydropyridines and unsaturated substrates. Experimental studies and DFT calculations provide mechanistic support for a concerted intermolecular aryne ene process, which may have implications for NAD(P)H model reactions.