7 Electrochemically Generated Nitrogen-Centered Radicals
Book
Editor: Ackermann, L.
Title: Electrochemistry in Organic Synthesis
Print ISBN: 9783132442122; Online ISBN: 9783132442146; Book DOI: 10.1055/b000000126
1st edition © 2022. Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart
Subjects: Organic Chemistry;Chemical Reactions, Catalysis;Organometallic Chemistry;Laboratory Techniques, Stoichiometry
Science of Synthesis Reference Libraries
Parent publication
Title: Science of Synthesis
DOI: 10.1055/b-00000101
Series Editors: Fürstner, A. (Editor-in-Chief); Carreira, E. M.; Faul, M.; Kobayashi, S.; Koch, G.; Molander, G. A.; Nevado, C.; Trost, B. M.; You, S.-L.
Type: Multivolume Edition
Abstract
Nitrogen-centered radicals are versatile reactive intermediates for organic synthesis. This chapter describes recent progress in the electrochemical generation and reactions of nitrogen-centered radicals. Under electrochemical conditions, various nitrogen-centered radicals are generated through electrolysis of readily available precursors such as N—H bonds or azides. These reactive intermediates undergo addition reactions to π-systems or hydrogen-atom abstraction to generate various nitrogen-containing compounds.
Key words
organic electrochemistry - electrosynthesis - electrocatalysis - nitrogen-centered radicals - radical reactions - heterocycles - carbon—nitrogen bond formation - oxidation - cyclization-
9 Zhang W, Wang F, McCann SD, Wang D, Chen P, Stahl SS, Liu G. Science (Washington, D. C.) 2016; 353: 1014
-
28 Hou Z.-W, Mao Z.-Y, Zhao H.-B, Melcamu YY, Lu X, Song J, Xu H.-C. Angew. Chem. Int. Ed 2016; 55: 9168
-
32 Lv S, Han X, Wang J.-Y, Zhou M, Wu Y, Ma L, Niu L, Gao W, Zhou J, Hu W, Cui Y, Chen J. Angew. Chem. Int. Ed 2020; 59: 11583
-
34 Li J.-S, Yang P.-P, Xie X.-Y, Jiang S, Tao L, Li Z.-W, Lu C.-H, Liu W.-D. Adv. Synth. Catal 2020; 362: 1977
-
50 Shono T, Matsumura Y, Katoh S, Takeuchi K, Sasaki K, Kamada T, Shimizu R. J. Am. Chem. Soc 1990; 112: 2368
-
60 Siu JC, Sauer GS, Saha A, Macey RL, Fu N, Chauviré T, Lancaster KM, Lin S. J. Am. Chem. Soc 2018; 140: 12511