Diversification of acridinium photocatalysts: Property tuning and reactivity in model reactions

IF 1.5 4区 化学 Q3 CHEMISTRY, ORGANIC Tetrahedron Letters Pub Date : 2025-03-22 DOI:10.1016/j.tetlet.2025.155546
Jason Y. Wang , Flora Fan , Madeline E. Ruos , Leticia Adao Gomes , Mimi Lavin , Thomas J. O'Connor , Steven A. Lopez , Abigail G. Doyle
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Abstract

Herein, we describe the discovery and characterization of multiple N-(hetero)aryl, N-benzyl and N-alkyl derivatives of 9-mesityl-3,6-di-tert-butyl-10-phenyl acridinium photocatalyst. The catalytic performances of these catalysts as photo-oxidant or photo-reductant (via in situ generated acridine radical) were compared in three model reactions. We also identified improved catalytic conditions for a previous cyanoarene-catalyzed nucleophilic amination reaction using a synthesized N-cycloheptyl acridinium catalyst (up to 98 % yield).

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吖啶光催化剂的多样化:性质调整和模型反应的反应性
本文描述了9-甲基亚基-3,6-二叔丁基-10-苯基吖啶鎓光催化剂的多个N-(杂)芳基、N-苄基和N-烷基衍生物的发现和表征。在三个模型反应中比较了这些催化剂作为光氧化剂和光还原剂(通过原位生成吖啶自由基)的催化性能。我们还发现,使用合成的n -环庚基吖啶鎓催化剂,改进了先前的氰芳烃催化的亲核胺化反应的催化条件(产率高达98%)。
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来源期刊
Tetrahedron Letters
Tetrahedron Letters 化学-有机化学
CiteScore
3.50
自引率
5.60%
发文量
521
审稿时长
28 days
期刊介绍: Tetrahedron Letters provides maximum dissemination of outstanding developments in organic chemistry. The journal is published weekly and covers developments in techniques, structures, methods and conclusions in experimental and theoretical organic chemistry. Rapid publication of timely and significant research results enables researchers from all over the world to transmit quickly their new contributions to large, international audiences.
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