Cobalt‐Catalyzed C(sp<sup>2</sup>)H Alkoxylation of Aromatic and Olefinic Carboxamides

Zhang, Linbao; Hao, Xin‐Qi; Zhang, Shou‐Kun; Liu, Zhan‐Jiang; Zheng, Xin‐Xiang; Gong, Jun‐Fang; Niu, Jun‐Long; Song, Mao‐Ping

doi:10.1002/anie.201409751

Cited by 221 publications

(80 citation statements)

References 81 publications

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“…In 2015, Niu and Song reported the first example of Co II ‐catalyzed alkoxylation of C(sp 2 )−H bonds in aromatic and olefinic carboxamides under basic and oxidizing conditions (Scheme ) . In the presence of Co(OAc) 2 ⋅ 4 H 2 O as the catalyst, various of benzamide substrates ( 78 ) and even olefinic carboxamides were tolerated to react with alcohols ( 79 ) for the formation of products ( 80 ) under mild conditions.…”

Section: C−h Activation/functionalizations Catalyzed By Using Coii Amentioning

confidence: 99%

High‐Valent‐Cobalt‐Catalyzed C−H Functionalization Based on Concerted Metalation–Deprotonation and Single‐Electron‐Transfer Mechanisms

et al. 2016

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C−H functionalization has been established as a powerful strategy for the commercial construction of organic molecules. This review encompasses the most recent advances in C−H activation catalyzed by earth‐abundant cobalt complexes, involving two types of fundamental reaction paths, that is, the concerted metalation–deprotonation (CMD) path associated with non‐oxidative C−H activation and the intermolecular single‐electron‐transfer (SET) path. Transformations catalyzed by high‐valent cobalt based on the two mechanisms and used in organic syntheses, including those involving C−C and C−X (X=O and N) bond formation, are herein presented.

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Section: C−h Activation/functionalizations Catalyzed By Using Coii Amentioning

confidence: 99%

High‐Valent‐Cobalt‐Catalyzed C−H Functionalization Based on Concerted Metalation–Deprotonation and Single‐Electron‐Transfer Mechanisms

et al. 2016

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“…Another bidentate directing group was applied by Niu and Song ( 158 , Scheme ), initially in an alkoxylation reaction towards 159 . The reaction conditions are quite similar to the ones reported by Daugulis.…”

Section: Cobalt‐catalyzed C−h Functionalization Reactionsmentioning

confidence: 78%

Direct Functionalization of C−H Bonds by Iron, Nickel, and Cobalt Catalysis

Pototschnig

Maulide

Schnürch

2017

Chemistry A European J

182

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Non-precious-metal-catalyzed reactions are of increasing importance in chemistry due to the outstanding ecological and economic properties of these metals. In the subfield of metal-catalyzed direct C-H functionalization reactions, recent years have shown an increasing number of publications dedicated to this topic. Nickel, cobalt, and last but not least iron, have started to enter a field which was long dominated by precious metals such as palladium, rhodium, ruthenium, and iridium. The present review article summarizes the development of iron-, nickel-, and cobalt-catalyzed C-H functionalization reactions until the end of 2016, and discusses the scope and limitations of these transformations.

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“…Next, we evaluated the potential of other known directing groups in assisting this transformation, including the perfluoroaniline, 2‐(pyridine‐2‐yl)‐isopropylamine, 2‐methylthioaniline, picolinamide, 2‐aminopyridine N ‐oxide, and 2‐(4,4‐dimethyl‐4,5‐dihydrooxazol‐2‐yl)aniline . We found that none of those groups were effective in directing the amination under the reaction conditions (see the Supporting Information).…”

Section: Methodsmentioning

confidence: 99%

Intermolecular Amination of Unactivated C(sp³)−H Bonds with Cyclic Alkylamines: Formation of C(sp³)−N Bonds through Copper/Oxygen‐Mediated C(sp³)−H/N−H Activation

Gou

Yang

Liu

et al. 2016

Chemistry A European J

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The first example of intermolecular amination of unactivated C(sp )-H bonds by cyclic alkylamines mediated by Cu(OAc) /O is reported. This method avoids the use of benzoyloxyamines as the aminating reagent, which are normally prepared from alkylamines in extra steps. A variety of unnatural β -amino acid analogues are synthesized by this simple and efficient procedure. This approach offers a solution to the previous unmet challenge of C(sp )-H/N-H activation for the formation of C(sp )-N bonds.

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Cobalt‐Catalyzed C(sp²)H Alkoxylation of Aromatic and Olefinic Carboxamides

Cited by 221 publications

References 81 publications

High‐Valent‐Cobalt‐Catalyzed C−H Functionalization Based on Concerted Metalation–Deprotonation and Single‐Electron‐Transfer Mechanisms

High‐Valent‐Cobalt‐Catalyzed C−H Functionalization Based on Concerted Metalation–Deprotonation and Single‐Electron‐Transfer Mechanisms

Direct Functionalization of C−H Bonds by Iron, Nickel, and Cobalt Catalysis

Intermolecular Amination of Unactivated C(sp³)−H Bonds with Cyclic Alkylamines: Formation of C(sp³)−N Bonds through Copper/Oxygen‐Mediated C(sp³)−H/N−H Activation

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Cobalt‐Catalyzed C(sp2)H Alkoxylation of Aromatic and Olefinic Carboxamides

Cited by 221 publications

References 81 publications

High‐Valent‐Cobalt‐Catalyzed C−H Functionalization Based on Concerted Metalation–Deprotonation and Single‐Electron‐Transfer Mechanisms

High‐Valent‐Cobalt‐Catalyzed C−H Functionalization Based on Concerted Metalation–Deprotonation and Single‐Electron‐Transfer Mechanisms

Direct Functionalization of C−H Bonds by Iron, Nickel, and Cobalt Catalysis

Intermolecular Amination of Unactivated C(sp3)−H Bonds with Cyclic Alkylamines: Formation of C(sp3)−N Bonds through Copper/Oxygen‐Mediated C(sp3)−H/N−H Activation

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Cobalt‐Catalyzed C(sp²)H Alkoxylation of Aromatic and Olefinic Carboxamides

Intermolecular Amination of Unactivated C(sp³)−H Bonds with Cyclic Alkylamines: Formation of C(sp³)−N Bonds through Copper/Oxygen‐Mediated C(sp³)−H/N−H Activation