4.8 Article

Cyclization of Alkyne-Azide with Isonitrile/CO via Self-Relay Rhodium Catalysis

Journal

ORGANIC LETTERS
Volume 18, Issue 5, Pages 908-911

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.5b03570

Keywords

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Funding

  1. National Natural Science Foundation of China [21302219]
  2. National S&T Pillar Program of China [2015BAK45B01]
  3. Fundamental Research Funds for the Central Universities (China Agricultural University) [2016QC040]
  4. Beijing National Laboratory of Molecular Sciences (BNLMS)

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A self-relay rhodium(I)-catalyzed cyclization of alkyne-azides with two sigma-donor/pi-acceptor ligands (isonitriles and CO) to form sequentially multiple-fused heterocycle systems via tandem nitrene transformation and aza-Pauson-Khand cyclization has been developed. In this approach, an intriguing chemoselective insertion process of isonitriles superior to CO was observed. This reaction provides an alternative strategy to synthesize functionalized pyrrolo[2,3-b]indole scaffolds.

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