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Yu, J.-Q.: 2015 Science of Synthesis, 3b: Catalytic Transformations via C-H Activation Vol. 2 DOI: 10.1055/sos-SD-218-00148
Catalytic Transformations via C—H Activation 2

2.8 C—N Bond Formation by Arene C—H Activation Using a Palladium Catalyst

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Editor: Yu, J.-Q.

Authors: Carreira, E. M.; Decicco, C. P.; Fuerstner, A.; Koch, G.; Molander, G. A.; Schaumann, E.; Shibasaki, M.; Thomas, E. J.; Trost, B. M.

Title: Catalytic Transformations via C-H Activation Vol. 2

Print ISBN: 9783132057210; Online ISBN: 9783132404137; Book DOI: 10.1055/b-004-129675

2015 © 2015 Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart

Subjects: Organic Chemistry

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Parent publication

Title: Science of Synthesis

DOI: 10.1055/b-00000101

Type: Multivolume Edition

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Abstract

The search for methodologies allowing C(sp2)—N bond formation is of utmost interest as the arylamine motif is ubiquitous in nature and life and material sciences. This chapter focuses on palladium-catalyzed arene C—H activation for the direct amination of C(sp2)—H bonds, generally under oxidizing conditions. These processes mainly allow the efficient introduction of carboxamides and sulfonamides, but the insertion of an amino group is also possible. Intramolecular transformations lead to the formation of either five-membered rings, such as carbazoles, indole derivatives, and benzo-fused nitrogen heterocycles, or six-membered rings, such as quinolinones and phenanthridinones. On the other hand, intermolecular reactions occur with complete regioselectivity, generally ortho to an appropriate directing group, which can be an oxime, a ketone, a carboxylic acid, or an amide.

Key words

palladium - arylamines - amination - intramolecular - intermolecular - regioselectivity - chemoselectivity - directing groups - carboxamides - sulfonamides - oxidants - heterocycles - carbazoles - indoles - dihydroindoles - oxindoles - benzimidazoles - benzotriazoles - quinolinones - phenanthridinones
 
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