Precise Synthesis of Multisubstituted Indoles Enabled by Palladium/Norbornene Cooperative Catalysis

doi:10.6023/cjoc202511008

Abstract

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

Cite this article

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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