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Chinese Journal of Organic Chemistry >

2022 , Vol. 42 >Issue 10: 3390 - 3397

DOI: https://doi.org/10.6023/cjoc202206053

ARTICLES

Dirhodium/Xantphos-Catalyzed Tandem C—H Functionalization/Allylic Alkylation: Direct Access to 3-Acyl-3-allyl Oxindole Derivatives from N-Aryl-α-diazo-β-keto Amides

  • Fangjie Li ,
  • Bin Lu ,
  • Yang Liu ,
  • Xiaoming Wang
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  • a Hunan Provincial Key Laboratory of Tumor Microenvironment Responsive Drug Research, Hunan Province Cooperative Innovation Center for Molecular Target New Drug Study, School of Pharmacology, Hengyang Medical School, University of South China, Hengyang, Hunan 421001
    b State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032
    c School of Chemistry and Materials Science, Hangzhou Institute for Advanced Study, University of Chinese Academy of Sciences, Hangzhou 310024
* Corresponding authors. E-mail: ;
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Received date: 2022-06-28

  Revised date: 2022-08-26

  Online published: 2022-09-09

Supported by

National Natural Science Foundation of China(21821002)

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Abstract

A novel [Rh2]/Xantphos-catalyzed one-pot sequence for the synthesis of diverse 3-acyl-3-allyl oxindole derivatives from easily available N-aryl-α-diazo-β-keto amides and allylic compounds has been developed. The notable features of this work include ease of operation, mild reaction conditions, good functional group compatibility and facile diversification of the products. Preliminary mechanistic studies indicate a tandem carbene-induced C—H functionalization and Rh(II)/Xantphos catalyzed allylic alkylation process. Moreover, the choice of Xantphos as the ligand is critical to enable the allylic alkylation process in this catalysis.

Key words： dirhodium(II); diazo compounds; oxindoles; quaternary centers; relay catalysis

Cite this article

Fangjie Li , Bin Lu , Yang Liu , Xiaoming Wang . Dirhodium/Xantphos-Catalyzed Tandem C—H Functionalization/Allylic Alkylation: Direct Access to 3-Acyl-3-allyl Oxindole Derivatives from N-Aryl-α-diazo-β-keto Amides[J]. Chinese Journal of Organic Chemistry, 2022 , 42(10) : 3390 -3397 . DOI: 10.6023/cjoc202206053

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