C4-Methylation and C4-Methylation/3,2-Carbonyl Migration of Indoles via Steric Control

doi:10.6023/cjoc202510028

Abstract

The development of methylation protocol has attracted intense attention owing to “magic methyl effect” in drug discovery. Meanwhile, the indole scaffold is prevalence in the natural products and pharmacaphores. Despite the advances in other site selective methylation, there is scarce reports for C4 methylation of indoles and combination of a carbonyl group rearrangement with C-H methylation on indole ring. Herein, we reported C4 methylation of indoles and steric controlled C4-methylation/carbonyl group dancing reaction. The large steric hindrance at carbonyl group facilitates the carbonyl group migration, which provides a straightforward protocol for synthesis of C2/ C4 disubstituted indoles.

Key words: methylation, carbonyl group dancing, Pd catalysis, magic methyl effect

Cite this article

Henan Xie, Yaohang Cheng, Guanghui An. C4-Methylation and C4-Methylation/3,2-Carbonyl Migration of Indoles via Steric Control[J]. Chinese Journal of Organic Chemistry, doi: 10.6023/cjoc202510028.

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位阻调控的吲哚C4位甲基化和C4甲基化/羰基重排反应