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Fensterbank, L.  et al.: 2021 Science of Synthesis, 2020/4: Free Radicals: Fundamentals and Applications in Organic Synthesis 1 DOI: 10.1055/sos-SD-234-00262
Free Radicals: Fundamentals and Applications in Organic Synthesis 1

1.12 Intermolecular Radical C—H Functionalization

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Book

Editors: Fensterbank, L. ; Ollivier, C.

Authors: André-Joyaux, E.; Bellanger, C.; Bertrand, M. P.; Besson, E. ; Bietti, M.; Braïda, B.; Cahoon, S. B.; Casano, G.; Chelli, S.; Chen, Y.; Chiba, S. ; Dénès, F. ; Derat, E.; Gastaldi, S. ; Gnägi, L.; Kaga, A.; Lakhdar, S. ; Liu, D.; Lu, X.-L.; Maestri, G. ; Melendez, C.; Ouari, O. ; Renaud, P. ; Rovis, T.; Serafino, A.; Shirakawa, E. ; Soulard, V.; Treacy, S. M.; Wang, B.; Wang, Y.-F.; Yoon, T. P.; Yorimitsu, H.; Zhang, F.-L.; Zhang, J.; Zhang, X.

Title: Free Radicals: Fundamentals and Applications in Organic Synthesis 1

Print ISBN: 9783132435520; Online ISBN: 9783132435537; Book DOI: 10.1055/b000000087

1st edition © 2021. 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.; Fürstner, A.; Carreira, E. M.; Faul, M.; Kobayashi, S.; Koch, G.; Molander, G. A.; Nevado, C.; Trost, B. M.; You, S.-L

Type: Multivolume Edition

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Abstract

The generation of carbon-centered radicals via intermolecular hydrogen-atom transfer (HAT) from C—H bonds to an abstracting species (HAT reagent) represents a significant challenge in terms of reactivity, site-selectivity and stereoselectivity. The radical species resulting from such a transfer can then engage in carbon—carbon or carbon—heteroatom bond formation, possibly through the intervention of transition-metal catalysts, leading to a variety of functionalized products. This chapter aims to provide the reader with useful guidelines to understand, predict, and design selective radical transformations based upon initial HAT from a C—H bond coupled to different radical-capture strategies. A selection of examples that illustrate different approaches to implement HAT reactions in synthetically useful procedures are presented.

Key words

radicals - C—H bond activation - radical reactions - hydrogen-atom transfer (HAT) - regioselectivity - halogenation - hydroxylation - amination - carbon–carbon coupling - iridium complexes - iron complexes - nickel complexes - hydrocarbons
 
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