4.8 Article

Regioselective Formal [4+2] Cycloadditions of Enaminones with Diazocarbonyls through Rh-III-Catalyzed C-H Bond Functionalization

Journal

ORGANIC LETTERS
Volume 20, Issue 13, Pages 3975-3979

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.8b01540

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Funding

  1. Natural Science Foundation of Jiangsu Province [BK20171463]
  2. State Key Program of National Natural Science Foundation of China [21432009]
  3. Jiangsu students' project for innovation and entrepreneurship training program [201810291045Z]
  4. SICAM Scholarship by Jiangsu National Synergetic Innovation Center for Advanced Materials
  5. Nanyang Technological University
  6. SICAM Fellowship by Jiangsu National Synergetic Innovation Center for Advanced Materials
  7. Nanjing Tech University

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A regioselective formal [4 + 2] cycloaddition for the assembly of highly functionalized benzene rings was successfully developed. In this reaction, olefinic C-H bond functionalization/cyclization cascade reaction followed by rearomatization led to the desired molecules in one step under mild reaction conditions. This protocol also displays a broad substrate scope and good tolerance to a wide range of functional groups. Additionally, the potential utility for the synthesis of highly conjugated polybenzenes and diversification of natural products was also demonstrated.

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