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Yu, J.-Q.: 2016 Science of Synthesis, 3a: Catalytic Transformations via C—H Activation 1 DOI: 10.1055/sos-SD-217-00074
Catalytic Transformations via C—H Activation 1

1.1.5 Vinylation Using a Palladium Catalyst

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Book

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 1

Subtitle: C-C, C-N, C-O, C-Hal, and C-B Bond Formation

Print ISBN: 9783131711311; Online ISBN: 9783132403413; Book DOI: 10.1055/b-003-129295

2016 © 2016 Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart

Subjects: Organic Chemistry;Chemical Reactions, Catalysis;Organometallic Chemistry;Laboratory Techniques, Stoichiometry

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Parent publication

Title: Science of Synthesis

DOI: 10.1055/b-00000101

Type: Multivolume Edition

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Abstract

This chapter covers methods for the vinylation of non-heteroaromatic arene C—H bonds with palladium catalysts. Both oxidative methods (dehydrogenative coupling of an arene with an alkene) and direct arylation methods (coupling of an arene with a vinyl halide or equivalent) are discussed. In many cases, directing groups are used to enhance reactivity and ensure site-selective vinylation. Examples of non-directed cases are also discussed. These vinylation methods are advantageous over other cross-coupling methods since pre-activation of the arene component (via an aryl halide or arylmetal species) is not necessary.

Key words

C—H activation - C—H functionalization - styrenes - acrylates - palladium catalysts - vinylation - alkenylation - cross coupling - catalysis - oxidation - oxidative coupling - direct arylation
 
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