钯/降冰片烯协同催化精准合成多取代吲哚

doi:10.6023/cjoc202511008

摘要/Abstract

多取代吲哚化合物是自然界中广泛分布的一类杂环化合物,大部分具有重要的生物活性．然而,吲哚丰富的化学反应性导致多取代吲哚的精准高效合成存在较大的挑战．本文报道了以单官能化吲哚为底物、烷基卤化物和烯烃为反应试剂,基于钯/降冰片烯协同催化策略,高位点选择性和高区域选择性合成复杂多取代吲哚衍生物．该合成方法具有较广的底物适用范围,可克级规模反应．此外,该反应具有良好的官能团兼容性,为多取代吲哚产物的进一步转化提供了可能．值得一提的是,从在机理上推断,该反应经历了关键的六元环钯中间体,进而实现了吲哚的跨环C—H键活化和多位点修饰．

关键词: 多取代吲哚, 钯/降冰片烯, 位点选择性, 区域选择性, 六元环钯中间体

Multisubstituted indoles are a class of heterocyclic compounds widely distributed in nature, and most of them exhibit significant biological activities．However, the rich chemical reactivity of indoles poses significant challenges for the precise and efficient synthesis of multisubstituted indoles．This article reports the highly site-selective and regioselective synthesis of complex multisubstituted indoles via a palladium/norbornene cooperative catalysis strategy, with readily available monofunctionalized indoles, alkyl halides, and alkenes as the building blocks．This method features broad substrate scope and good scalability． In addition, the reaction demonstrates excellent functional group tolerance, thus offering opportunities for the further modification of the obtained multisubstituted indole products．It is worth mentioning that a key six-membered palladacycle intermediate is presumed to exist in the reaction mechanism, enabling remote modifications of indole across the ring．

Key words: multisubstituted indole, Pd/NBE, site-selectivity, regioselectivity, six-membered palladacycle

引用此文

付雪鹏, 汪建树, 陈树清, 程鸿刚, 周强辉. 钯/降冰片烯协同催化精准合成多取代吲哚[J]. 有机化学, doi: 10.6023/cjoc202511008.

Fu Xuepeng, Wang Jian-Shu, Chen Shuqing, Cheng Hong-Gang, Zhou Qianghui. Precise Synthesis of Multisubstituted Indoles Enabled by Palladium/Norbornene Cooperative Catalysis[J]. Chinese Journal of Organic Chemistry, doi: 10.6023/cjoc202511008.

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