C4-H indole functionalisation: precedent and prospects.

C4-H indole functionalisation: precedent and prospects.
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DOI:
10.1039/c7sc05336c
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发表时间:
2018-05-14
期刊:
影响因子:
8.4
通讯作者:
Pilarski LT
Pilarski LT
中科院分区:
化学1区
文献类型:
--
作者:
Kalepu J;Gandeepan P;Ackermann L;Pilarski LT

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这篇透视文章追溯了现代方法的发展,以功能化吲哚C4-H键。C4-修饰的吲哚在天然产物合成、材料科学以及作物保护和制药工业中具有重要的生物活性和功能性化合物。传统上,它们的合成主要涉及苛刻的化学计量金属化和自由基反应。然而,过渡金属催化的C-H活化最近已经发展成为吲哚在C4-H位置的后期多样化的有力策略。现代光氧化还原、酶催化和贵金属催化代表了在温和反应条件下开发具有挑战性的C-C和C-Het键形成转化的关键刺激。在这里,我们讨论了这些方法的演变和应用,以逐步经济的转变,否则惰性C4-H键到2017年12月。
This Perspective article traces the evolution of modern approaches to functionalise the indole C4–H bond. C4-decorated indoles feature in a plethora of bioactive and functional compounds of importance to natural product synthesis, material sciences, as well as crop protection and pharmaceutical industries. Traditionally, their syntheses largely involved harsh stoichiometric metalations and radical reactions. However, transition metal catalysed C–H activation has recently evolved into a powerful strategy for the late-stage diversification of indoles at the C4–H position. Modern photoredox, enzymatic and precious transition metal catalysis represent the key stimuli for developing challenging C–C and C–Het bond forming transformations under mild reaction conditions. Herein, we discuss the evolution and application of these methods for the step-economical transformations of otherwise inert C4–H bonds up to December 2017.
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