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Bis(amino)cyclopropenium Ion as a Hydrogen-Bond Donor Catalyst for 1,6-Conjugate Addition Reactions
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2021-03-15 , DOI: 10.1021/acs.joc.0c02940
Pavit Kumar Ranga 1 , Feroz Ahmad 1 , Prashant Nager 1 , Prabhat Singh Rana 1 , Ramasamy Vijaya Anand 1
Affiliation  

The catalytic application of the bis(amino)cyclopropenium ion has been investigated in conjugate addition reactions. The hydrogen atom, which is attached to the cyclopropene ring of bis(amino)cyclopropenium salts, is moderately acidic and can potentially serve as a hydrogen-bond donor catalyst in some organic transformations. This hypothesis has been successfully realized in the 1,6-conjugate addition reactions of p-quinone methides with various nucleophiles such as indole, 2-naphthol, thiols, phenols, and so forth. The spectroscopic studies (NMR and UV–vis) as well as the deuterium isotope labeling studies clearly revealed that the hydrogen atom (C–H) that is present in the cyclopropene ring of the catalyst is indeed solely responsible for catalyzing these transformations. In addition, these studies also strongly indicate that the C–H hydrogen of the cyclopropene ring activates the carbonyl group of the p-quinone methide through hydrogen bonding.

中文翻译:

双(氨基)环丙烯离子作为氢键供体催化剂,用于1,6-共轭加成反应

在共轭加成反应中已经研究了双(氨基)环丙烯离子的催化应用。连接到双(氨基)环丙烯盐的环丙烯环上的氢原子是中等酸性的,在某些有机转化中可以潜在地用作氢键供体催化剂。该假设已在p的1,6-共轭加成反应中成功实现-醌甲基化物与各种亲核试剂,例如吲哚,2-萘酚,硫醇,酚等。光谱研究(NMR和UV-vis)以及氘同位素标记研究清楚地表明,催化剂的环丙烯环中存在的氢原子(CH)确实是催化这些转化的唯一原因。此外,这些研究还强烈表明,环丙烯环的C–H氢通过氢键激活了对醌甲基化物的羰基。
更新日期:2021-04-02
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