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可见光促进2-异氰基萘与元素硫和胺的串联偶联以构建萘并[2,1-d]噻唑-2-胺

Visible-Light-Promoted Cascade Coupling of 2-Isocyanonaphthalenes with Elemental Sulfur and Amines to Construct Naphtho[2,1-d]thiazol-2-Amines.

作者信息

Ding Hongyu, Shi Siyu, Hou Yanan, Cui Wenxiu, Sun Rong, Lv Yufen, Yue Huilan, Wei Wei, Yi Dong

机构信息

Key Laboratory of Catalytic Conversion and Clean Energy in Universities of Shandong Province, Department School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu, 273165, Shandong, P.R.China.

Qinghai Provincial Key Laboratory of Tibetan Medicine Research, CAS Key Laboratory of Tibetan Medicine Research, Northwest Institute of Plateau Biology, Qinghai, 810008, P.R.China.

出版信息

Chemistry. 2024 May 14;30(27):e202400719. doi: 10.1002/chem.202400719. Epub 2024 Mar 22.

Abstract

A visible-light-induced strategy has been explored for the synthesis of naphtho[2,1-d]thiazol-2-amines through ortho-C-H sulfuration of 2-isocyanonaphthalenes with elemental sulfur and amines under external photocatalyst-free conditions. This three-component reaction, which utilizes elemental sulfur as the odorless sulfur source, molecular oxygen as the clean oxidant, and visible light as the clean energy source, provides a mild and efficient approach to construct a series of naphtho[2,1-d]thiazol-2-amines. Preliminary mechanistic studies indicated that visible-light-promoted photoexcitation of reaction intermediates consisting of thioureas and DBU might be involved in this transformation.

摘要

已经探索了一种可见光诱导的策略,用于在无外部光催化剂的条件下,通过2-异氰基萘与元素硫和胺的邻位C-H硫化反应合成萘并[2,1-d]噻唑-2-胺。这种三组分反应利用元素硫作为无臭硫源、分子氧作为清洁氧化剂、可见光作为清洁能源,为构建一系列萘并[2,1-d]噻唑-2-胺提供了一种温和有效的方法。初步机理研究表明,由硫脲和DBU组成的反应中间体的可见光促进光激发可能参与了这种转化。

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