Rhodium(III)-Catalyzed Regioselective C-H Allylation and Prenylation of Indoles at C4-Position

作者：Zhang, Shang-Shi^*; Liu, Yan-Zhi; Zheng, Yi-Chuan; Xie, Hui; Chen, Shao-Yong; Song, Jia-Lin; Shu, Bing^*

来源：Advanced Synthesis and Catalysis, 2022, 364(1): 64-70.

DOI：10.1002/adsc.202100882

• Rh(III)-catalyzed
• C-H allylation
• C-H prenylation
• C4-selective functionalization
• branched allyl indoles

Herein, Rh(III)-catalyzed C4-selective C-H allylation and prenylation of indoles by using a weak carbonyl coordination directing group have been reported. By employing 5-methylene-1,3-dioxan-2-ones, 4-vinyl-1,3-dioxolan-2-ones and 2-methyl-2,3-butadiene as scalable cross-coupling partners, these divergent synthesis protocols proceed smoothly under redox-neutral reaction conditions, delivering various allylated and prenylated indoles in moderate to satisfied yields. This transformation exhibits high functional-groups compatibility and broad substrate scope. Scale-up experiment and mechanistic studies were also accomplished.

• 单位
  广东药学院