Photochemical and Electrochemical Applications of Proton-Coupled Electron Transfer in Organic Synthesis.
Photochemical and Electrochemical Applications of Proton-Coupled Electron Transfer in Organic Synthesis.
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DOI：
10.1021/acs.chemrev.1c00374
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发表时间：
2022-01-26
期刊：
影响因子：
62.1
通讯作者：
Knowles RR
中科院分区：
文献类型：
--
作者：
Murray PRD;Cox JH;Chiappini ND;Roos CB;McLoughlin EA;Hejna BG;Nguyen ST;Ripberger HH;Ganley JM;Tsui E;Shin NY;Koronkiewicz B;Qiu G;Knowles RR
本文综述了多位质子耦合电子转移（MS-PCET）在有机合成中的光化学和电化学应用。MS-质子交换是氧化还原机制，其中电子和质子一起交换，通常在协调的基本步骤中。因此，MS-PCET可以用作均裂键活化的非经典机制，提供直接从各种常见有机官能团生成合成有用的自由基中间体的机会。我们提出了一个介绍MS-PCET和从业者的反应设计指南，重点是独特的充满活力和选择性的特点，这类反应。然后，我们提出的章节氧化N-H，O-H，S-H，和C-H键均裂方法，为相应的中性自由基物种的产生。然后，涉及羰基，亚胺，其他X=Y π-系统和杂芳烃，其中中性酮基，α-氨基和杂芳烃衍生自由基的还原PCET活化的章节可以产生。最后，我们提出的MS-PCET在不对称催化和在材料和设备应用的应用章节。在每一章中，我们通过经历均裂的官能团进行细分，然后通过促进转化的类型进行细分。列出了2020年12月底之前发表的方法。
We present here a review of the photochemical and electrochemical applications of multi-site proton-coupled electron transfer (MS-PCET) in organic synthesis. MS-PCETs are redox mechanisms in which both an electron and a proton are exchanged together, often in a concerted elementary step. As such, MS-PCET can function as a non-classical mechanism for homolytic bond activation, providing opportunities to generate synthetically useful free radical intermediates directly from a wide variety of common organic functional groups. We present an introduction to MS-PCET and a practitioner’s guide to reaction design, with an emphasis on the unique energetic and selectivity features that are characteristic of this reaction class. We then present chapters on oxidative N–H, O–H, S–H, and C–H bond homolysis methods, for the generation of the corresponding neutral radical species. Then, chapters for reductive PCET activations involving carbonyl, imine, other X=Y π-systems, and heteroarenes, where neutral ketyl, α-amino, and heteroarene-derived radicals can be generated. Finally, we present chapters on the applications of MS-PCET in asymmetric catalysis and in materials and device applications. Within each chapter, we subdivide by the functional group undergoing homolysis, and thereafter by the type of transformation being promoted. Methods published prior to the end of December 2020 are presented.
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DOI：
10.1039/c3cc46391e
发表时间：
2013-11-25
期刊：
Chemical communications (Cambridge, England)
影响因子：
--
作者：
Wang D;Que L Jr
通讯作者：
Que L Jr
影响因子：
15
作者：
ANDRIEUX, CP;BLOCMAN, C;SAVEANT, JM
通讯作者：
SAVEANT, JM
影响因子：
3.7
作者：
Alligrant, Timothy M.;Alvarez, Julio C.
通讯作者：
Alvarez, Julio C.
影响因子：
--
作者：
Ahmad, Mamshad;Masohan, Asha;Sawhney, S. S.
通讯作者：
Sawhney, S. S.
DOI：
10.1139/v95-042
发表时间：
1995-03-01
期刊：
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE
影响因子：
--
作者：
ARNOLD, DR;DU, XY;CHEN, J
通讯作者：
CHEN, J