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噻吩稠合杂芳烃体系的内氧化剂诱导的串联双杂芳环化构建。

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

机构信息

Key Laboratory for Green Organic Synthesis and Application of Hunan Province, Key Laboratory of Environmentally Friendly Chemistry and Application of Ministry of Education, College of Chemistry , Xiangtan University , Xiangtan 411105 , China.

出版信息

Org Lett. 2018 Aug 17;20(16):4917-4920. doi: 10.1021/acs.orglett.8b02049. Epub 2018 Aug 6.

DOI:10.1021/acs.orglett.8b02049
PMID:30080418
Abstract

A concise access to thiophene-fused polycyclic π-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.

摘要

描述了一种简洁的噻吩稠合多环π共轭体系的方法。通过新颖的双杂环并合一锅法,在简便的铜催化体系中,甲氧基芳酮乙酸酯、芳醛和元素硫高效地组装在一起,得到稠合噻吩[3,2- d]噻唑基序。该反应体系的稳健性体现在一锅操作中显著的从简单到复杂的转化、高产克级规模合成以及在高性能光电材料合成中的潜在应用。

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