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Transition-metal-catalyzed site-selective C7-functionalization of indoles: advancement and future prospects
Chemical Communications ( IF 4.9 ) Pub Date : 2018-12-05 00:00:00 , DOI: 10.1039/c8cc04116d
Tariq A. Shah 1, 2, 3, 4 , Pinaki Bhusan De 1, 2, 3, 4 , Sourav Pradhan 1, 2, 3, 4 , Tharmalingam Punniyamurthy 1, 2, 3, 4
Affiliation  

C7-Decorated indoles are important structural motifs present in a plethora of bioactive and pharmaceutical compounds. Early stage developments for C7 modifications were realized through directed metallation (DOM) and subsequent quenching with suitable electrophiles or by halogenation with Cu(II) halides. Direct C-7 functionalization of indoles is comparatively difficult compared to functionalization at C-2 and C-3 positions owing to the inherent reactivity of the pyrrole-type ring. However, recently transition-metal-catalyzed auxiliary assisted site-selective C-7 functionalization of indoles has emerged as an elegant synthetic tool for carbon–carbon and carbon–heteroatom bond formation to diversify the indoles. This article covers the advancement, application and mechanistic underpinnings of the evolved transformations of the otherwise inert C7–H bond up to October 2018.

中文翻译:

吲哚的过渡金属催化位点选择性C7-官能化:进展和未来前景

C7装饰的吲哚是存在于大量生物活性和药物化合物中的重要结构基序。通过定向金属化(DOM)并随后使用合适的亲电试剂进行淬灭或通过用Cu(II)进行卤化,实现了C7修饰的早期开发。)卤化物。由于吡咯型环的固有反应性,与C-2和C-3位置的功能化相比,吲哚的直接C-7功能化相对困难。然而,最近,吲哚的过渡金属催化辅助位点选择性C-7官能化已经成为形成碳-碳和碳-杂原子键使吲哚多样化的一种优雅的合成工具。本文涵盖了直到2018年10月否则呈惰性的C7–H键的演化转变的进展,应用和机理基础。
更新日期:2018-12-05
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