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Oxidative Synthesis of 1,3-Diarylphenanthro[9,10-c]thiophenes and their Aerobic Photoconversion to 9,10-Diaroylphenanthrenes
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2024-07-12 , DOI: 10.1002/adsc.202400569
Sankarrao Mahanthi 1 , Sudhakar Maddala 1 , Venkatakrishnan Parthasarathy 1
Affiliation  

Our study introduces a streamlined oxidative method for synthesizing 1,3-diarylphenanthro[9,10-c]thiophenes, and their subsequent oxidative cleavage to yield 9,10-diaroylphenanthrenes. Harnessing an optimized aerobic photochemical transformation, we showcase broad substrate scope and tolerance to various photosensitive functional groups. Our mechanistic investigations unveil the pivotal role of singlet oxygen, providing intriguing insights into the reaction pathway. The synthesized 9,10-diaroylphenanthrenes serve as versatile building blocks for nitrogen-containing heterocycles, dibenzoannulated phthalazines, that are promising compounds with diverse functionalities. Offering mild conditions, and broad applicability, our synthetic strategy is useful for organic synthesis and chemical biology exploration.



中文翻译:


1,3-二芳基菲[9,10-c]噻吩的氧化合成及其有氧光转化为9,10-二芳酰基菲



我们的研究介绍了一种合成 1,3-二芳基菲[9,10- c ]噻吩的简化氧化方法,以及随后的氧化裂解产生 9,10-二芳酰基菲。利用优化的有氧光化学转化,我们展示了广泛的底物范围和对各种光敏官能团的耐受性。我们的机理研究揭示了单线态氧的关键作用,为反应途径提供了有趣的见解。合成的 9,10-二芳酰基菲可作为含氮杂环、二苯并环二氮杂萘的通用结构单元,是具有多种功能的有前途的化合物。我们的合成策略提供温和的条件和广泛的适用性,可用于有机合成和化学生物学探索。

更新日期:2024-07-12
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