Journal ArticleDOI
Copper-Catalyzed Aerobic Oxidative C ? H Functionalizations: Trends and Mechanistic Insights
TLDR
This work has reported several recently reported Cu-catalyzed C-H oxidation reactions that feature substrates that are electron-deficient or appear unlikely to undergo single-electron transfer to copper(II), and evidence has been obtained for the involvement of organocopper(III) intermediates in the reaction mechanism.Abstract:
The selective oxidation of C-H bonds and the use of O(2) as a stoichiometric oxidant represent two prominent challenges in organic chemistry. Copper(II) is a versatile oxidant, capable of promoting a wide range of oxidative coupling reactions initiated by single-electron transfer (SET) from electron-rich organic molecules. Many of these reactions can be rendered catalytic in Cu by employing molecular oxygen as a stoichiometric oxidant to regenerate the active copper(II) catalyst. Meanwhile, numerous other recently reported Cu-catalyzed C-H oxidation reactions feature substrates that are electron-deficient or appear unlikely to undergo single-electron transfer to copper(II). In some of these cases, evidence has been obtained for the involvement of organocopper(III) intermediates in the reaction mechanism. Organometallic C-H oxidation reactions of this type represent important new opportunities for the field of Cu-catalyzed aerobic oxidations.read more
Citations
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Journal ArticleDOI
Thioether-Directed C4-Selective C-H Acylmethylation of Indoles Using α-Carbonyl Sulfoxonium Ylides.
TL;DR: An iridium-catalyzed C4-selective acylmethylation of indoles using α-carbonyl sulfoxonium ylides as carbene precursors is demonstrated, which exhibits high efficiency and broad functional group compatibility.
Journal ArticleDOI
Cobaltkatalysierte C‐H‐Thiolierung durch dehydrierende Kreuzkupplung
Journal ArticleDOI
Transient and Recyclable Halogenation Coupling (TRHC) for Isoflavonoid Synthesis with Site-Selective Arylation.
Jie-Ping Wan,Zhi Tu,Yuyun Wang +2 more
TL;DR: A transient and recyclable C-H iodination has been designed for the synthesis of isoflavonoids through the domino reactions of o-hydroxyphenyl enaminones and aryl boronic acids in the presence of catalytic KI and Pd catalyst, disclosing an intriguing new coupling protocol to forge the C-C bond in the virgin area between classical C-X (X=halogen) bond cross coupling and theC-H activation.
Journal ArticleDOI
Tandem-type Pd(II)-catalyzed oxidative Heck reaction/intramolecular C-H amidation sequence: a novel route to 4-aryl-2-quinolinones.
TL;DR: A novel catalytic method for synthesizing 4-aryl-2-quinolinones is reported, which involves two mechanistically independent, sequential Pd(II)-catalyzed reactions--the oxidative Heck reaction and the intramolecular C-H amidation.
Journal ArticleDOI
Copper-mediated C3-cyanation of indoles by the combination of amine and ammonium†
TL;DR: A copper-promoted C3-cyanation of both the free N-H and N-protected indoles by N,N,N',N'-tetramethyl-ethane-1,2-diamine and ammonium and the iminium ion represents a facile and safe procedure leading to 3-cyano indoles.
References
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Journal ArticleDOI
Palladium-Catalyzed Ligand-Directed C−H Functionalization Reactions
TL;DR: This is the first comprehensive review encompassing the large body of work in this field over the past 5 years, and will focus specifically on ligand-directed C–H functionalization reactions catalyzed by palladium.
Journal ArticleDOI
Palladium(II)-catalyzed C-H activation/C-C cross-coupling reactions: versatility and practicality.
TL;DR: A review of palladium-catalyzed coupling of CH bonds with organometallic reagents through a PdII/Pd0 catalytic cycle can be found in this paper.
Journal ArticleDOI
Catalytic dehydrogenative cross-coupling: forming carbon-carbon bonds by oxidizing two carbon-hydrogen bonds
Charles S. Yeung,Vy M. Dong +1 more
Journal ArticleDOI
Multicopper Oxidases and Oxygenases
TL;DR: Copper sites have historically been divided into three classes based on their spectroscopic features, which reflect the geometric and electronic structure of the active site: type 1 or blue copper, type 2 (T2) or normal copper, and type 3 (T3) or coupled binuclear copper centers.
Journal ArticleDOI
Rhodium-Catalyzed C-C Bond Formation via Heteroatom-Directed C-H Bond Activation
TL;DR: This review focuses on Rh-catalyzed methods for C-H bond functionalization, which have seen widespread success over the course of the last decade and are discussed in detail in the accompanying articles in this special issue of Chemical Reviews.
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