4.8 Article

Thiophene-Fused Heteroaromatic Systems Enabled by Internal Oxidant-Induced Cascade Bis-Heteroannulation

Journal

ORGANIC LETTERS
Volume 20, Issue 16, Pages 4917-4920

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.8b02049

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Funding

  1. National Natural Science Foundation of China [21602187, 21572194]
  2. Collaborative Innovation Center of New Chemical Technologies for Environmental Benignity and Efficient Resource Utilization
  3. Scientific Research Fund of Hunan Provincial Education Department [16B251]
  4. Hunan Provincial Natural Science Foundation of China [2017113299]

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A concise access to thiophene-fused polycyclic pi-conjugated systems is described. Methyl aromatic ketoxime acetates, aromatic aldehydes, and elemental sulfur are efficiently assembled in a facile copper-catalytic system through a novel cascade bis-heteroannulation to afford a fused thieno[3,2-d]thiazole motif. The robust nature of this reaction system is reflected by the remarkable simplicity-to-complexity transformation in a one-pot operation, high-yield gram-scale synthesis, and potential applications on the synthesis of high-performance optoelectronic materials.

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