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Ester dance reaction on the aromatic ring.
Science Advances ( IF 13.6 ) Pub Date : 2020-07-08 , DOI: 10.1126/sciadv.aba7614
Kaoru Matsushita 1 , Ryosuke Takise 1 , Kei Muto 1 , Junichiro Yamaguchi 1
Affiliation  

Aromatic rearrangement reactions are useful tools in the organic chemist’s toolbox when generating uncommon substitution patterns. However, it is difficult to precisely translocate a functional group in (hetero) arene systems, with the exception of halogen atoms in a halogen dance reaction. Here, we describe an unprecedented “ester dance” reaction: a predictable translocation of an ester group from one carbon atom to another on an aromatic ring. Specifically, a phenyl carboxylate substituent can be shifted from one carbon to an adjacent carbon on a (hetero) aromatic ring under palladium catalysis to often give a thermodynamically favored, regioisomeric product with modest to good conversions. The obtained ester moiety can be further converted to various aromatic derivatives through the use of classic and state-of-the-art transformations including amidation, acylations, and decarbonylative couplings.



中文翻译:

芳香环上的酯舞反应。

当产生不常见的取代模式时,芳香重排反应是有机化学家工具箱中的有用工具。然而,在(杂)芳烃系统中精确地转移官能团是很困难的,除了卤素舞蹈反应中的卤素原子之外。在这里,我们描述了一种前所未有的“酯舞”反应:酯基团从芳环上的一个碳原子到另一个碳原子的可预测易位。具体而言,在钯催化下,羧酸苯酯取代基可以从(杂)芳环上的一个碳转移到相邻的碳,通常会产生热力学有利的区域异构产物,并具有中等至良好的转化率。通过使用经典和最先进的转化(包括酰胺化、酰化和脱羰基偶联),获得的酯部分可以进一步转化为各种芳香族衍生物。

更新日期:2020-07-08
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