2.9 C—N Bond Formation by C—H Functionalization via Metal-Catalyzed Nitrene Insertion

N. Weldy; S. B. Blakey

doi:10.1055/sos-SD-218-00167

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Yu, J.-Q.: 2015 Science of Synthesis, 3b: Catalytic Transformations via C-H Activation 2 DOI: 10.1055/sos-SD-218-00167

Catalytic Transformations via C—H Activation 2

2.9 C—N Bond Formation by C—H Functionalization via Metal-Catalyzed Nitrene Insertion

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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 2

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

1st edition © 2015 Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart

Subjects: Organic Chemistry

Science of Synthesis Reference Libraries

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Title: Science of Synthesis

DOI: 10.1055/b-00000101

Type: Multivolume Edition

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Abstract

New routes for the formation of C—N bonds are important due to the prevalence of these bonds in complex natural products and molecules of pharmaceutical interest. Metallonitrene amination requires pre-oxidation of an amine, using precursors such as azides, N-(tosyloxy)carbamates, and iminoiodinanes. Binding of a transition-metal catalyst to the nitrene source gives the metallonitrene, which is capable of inserting into C—H bonds. Insertion may be made enantioselective in some systems by the use of a chiral metal complex. Most early examples of metallonitrene C—H amination focused on insertion into benzylic C—H bonds, but recently the substrate scope has been expanded to include aryl, vinyl, and even unactivated tertiary, secondary, and primary bonds.

Key words

amination - nitrenes - C—N bonds - enantioselectivity - rhodium catalysts - ruthenium catalysts - iridium catalysts - cobalt catalysts - iron catalysts

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