Strongly Oxidizing Thiapyrylium Salt for Organophotoredox Catalysis

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-05-01 DOI:10.1021/acs.orglett.5c01080

Mohamed R. El-kholany, Takeru Senoo, Asuka Mizutani, Hiroyoshi Takamura, Takayoshi Suzuki, Isao Kadota, Kenta Tanaka

引用次数: 0

Abstract

Photoredox catalysis has garnered significant attention in organic chemistry for its ability to promote chemical transformations under visible-light irradiation. To date, research on salt-based organophotoredox catalysts has mainly concentrated on the development of oxygen- and nitrogen-based catalysts such as acridinium and pyrylium salts, whereas sulfur-containing catalysts have received far less attention. Herein, we report a strongly oxidizing tert-butyl-substituted thiapyrylium organophotoredox catalyst (^tBu-TTPP) that exhibits a high excited-state reduction potential (E_1/2(C*/C^•–) = +2.23 V vs SCE) and can be activated by blue LEDs. The ^tBu-TTPP catalyst provided promising results in various photoredox reactions, such as radical-cation Diels–Alder reactions, trifluoromethylations, the [4 + 2] annulation of alkynes and thiophene, and the C–N cross-coupling of fluoroarenes, demonstrating its potential in photoredox catalysis.

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强氧化噻吩盐在有机光氧化还原催化中的应用

光氧化还原催化因其在可见光照射下促进化学转化的能力而引起了有机化学领域的广泛关注。迄今为止，盐基有机光氧化还原催化剂的研究主要集中在氧基和氮基催化剂如吖啶盐和吡啶盐的开发上，而含硫催化剂的研究很少。本文报道了一种强氧化性叔丁基取代噻吩基有机光氧化还原催化剂（tbuttpp），该催化剂具有高激发态还原电位（E1/2(C*/C•-)= +2.23 V vs SCE），可以被蓝色led激活。tbuttpp催化剂在各种光氧化还原反应中都有很好的效果，如自由基-阳离子Diels-Alder反应、三氟甲基化反应、炔和噻吩的[4 + 2]环化反应以及氟芳烃的C-N交叉偶联反应，显示了其在光氧化还原催化方面的潜力。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.