Cobalt-Catalyzed Carbon–Heteroatom Transfer Enables Regioselective Tricomponent 1,4-Carboamination DOI

Kaitong Zhuang,

Graham C. Haug, Yangyang Wang

и другие.

Journal of the American Chemical Society, Год журнала: 2024, Номер 146(12), С. 8508 - 8519

Опубликована: Фев. 21, 2024

Tricomponent cobalt(salen)-catalyzed carbofunctionalization of unsaturated substrates by radical-polar crossover has the potential to streamline access broad classes heteroatom-functionalized synthetic targets, yet reaction platform remained elusive, despite well-developed analogous hydrofunctionalizations mediated high-valent alkylcobalt intermediates. We report herein development a cobalt(salen) catalytic system that enables carbofunctionalization. The entails tricomponent decarboxylative 1,4-carboamination dienes and provides direct route aromatic allylic amines obviating preformed allylation reagents protection oxidation-sensitive amines. merges acridine photocatalysis with regioselective 1,4-carbofunctionalization facilitates radical polar phases coupling process, revealing critical roles reactants, as well ligand effects nature formal species on chemo- regioselectivity.

Язык: Английский

Coordination-assisted, transition-metal-catalyzed enantioselective desymmetric C–H functionalization DOI
Xin Yu, Zhuo‐Zhuo Zhang, Jun‐Long Niu

и другие.

Organic Chemistry Frontiers, Год журнала: 2022, Номер 9(5), С. 1458 - 1484

Опубликована: Янв. 1, 2022

Recent advances in transition-metal-catalyzed enantioselective desymmetric C–H functionalization are summarized.

Язык: Английский

Процитировано

46
Synthesis of Natural Products by C−H Functionalization of Heterocycless DOI
Yang Zhang, Michal Szostak

Chemistry - A European Journal, Год журнала: 2022, Номер 28(22)

Опубликована: Янв. 28, 2022

Total synthesis is considered by many as the finest combination of art and science. During last decades, several concepts were proposed for achieving perfect vision total synthesis, such atom economy, step or redox economy. In this context, C-H functionalization represents most powerful platform that has emerged in years, empowering rapid complex natural products enabling diversification bioactive scaffolds based on product architectures. review, we present an overview recent strategies towards heterocyclic enabled functionalization. Heterocycles represent common motifs drug discovery marketed drugs. The implementation heterocycles enables novel tactics construction core architectures, but also changes logic design retrosynthetic permits access to with enhanced biological activities.

Язык: Английский

Процитировано

42
Silver-catalyzed site-selective C(sp3)−H benzylation of ethers with N-triftosylhydrazones DOI Creative Commons
Zhaohong Liu, Hongwei Wang, Paramasivam Sivaguru

и другие.

Nature Communications, Год журнала: 2022, Номер 13(1)

Опубликована: Март 30, 2022

Abstract The insertion of carbenes into the α-C–H bonds ethers represents one most powerful approaches to access polysubstituted α-branched ethers. However, intermolecular carbene insertions remain challenging, since current are generally limited use toxic and potentially explosive α-diazocarbonyl compounds. We now report a silver-catalyzed benzylation using bench-stable N -triftosylhydrazones as safe convenient precursors. This approach is well suited for both inter- intramolecular deliver medicinally relevant homobenzylic 5–8-membered oxacycles in good yields. synthetic utility this strategy demonstrated by its easy scalability, broad scope with valuable functional groups, high regioselectivity, late-stage functionalization complex oxygen-containing molecules. relative reactivities different types silver C−H were also investigated experments DFT calculations.

Язык: Английский

Процитировано

42
Ruthenium(ii)-catalyzed synthesis of CF3-isoquinolinones via C–H activation/annulation of benzoic acids and CF3-imidoyl sulfoxonium ylides DOI

Si Wen,

Yu‐Qing Zhang,

Qingyu Tian

и другие.

Organic Chemistry Frontiers, Год журнала: 2022, Номер 9(16), С. 4388 - 4393

Опубликована: Янв. 1, 2022

The synthesis of 3-trifluoromethylisoquinolinones by a ruthenium( ii )-catalyzed C–H activation/annulation reaction benzoic acids and CF 3 -imidoyl sulfoxonium ylides has been achieved.

Язык: Английский

Процитировано

41
Functional-group translocation of cyano groups by reversible C–H sampling DOI
K. Chen,

Qingrui Zeng,

L. XIE

и другие.

Nature, Год журнала: 2023, Номер 620(7976), С. 1007 - 1012

Опубликована: Июнь 26, 2023

Язык: Английский

Процитировано

40
Synthetic applications of hydride abstraction reactions by organic oxidants DOI

Jenna L. Miller,

Jean‐Marc Lawrence,

Freddy O. Rodriguez del Rey

и другие.

Chemical Society Reviews, Год журнала: 2022, Номер 51(13), С. 5660 - 5690

Опубликована: Янв. 1, 2022

Organic oxidants, including quinones, oxoammonium ions, and trityl cations, abstract hydride ions to form carbocations. This review describes the mechanistic foundations for these processes vast array of their applications in synthesis.

Язык: Английский

Процитировано

39
The green chemistry paradigm in modern organic synthesis DOI
Sergei G. Zlotin, Ksenia S. Egorova, Valentine P. Ananikov

и другие.

Russian Chemical Reviews, Год журнала: 2023, Номер 92(12), С. RCR5104 - RCR5104

Опубликована: Дек. 1, 2023

After the appearance of green chemistry concept, which was introduced in vocabulary early 1990s, its main statements have been continuously developed and modified. Currently, there are 10–12 cornerstones that should form basis for an ideal chemical process. This review analyzes accumulated experience achievements towards design products processes reduce or eliminate use generation hazardous substances. The presents views leading Russian scientists specializing various fields this subject, including homogeneous heterogeneous catalysis, fine basic organic synthesis, electrochemistry, polymer chemistry, based on bio-renewable feedstocks energetic compounds materials. A new approach to quantitative evaluation environmental friendliness by authors is described. <br> bibliography includes 1761.

Язык: Английский

Процитировано

39
Preparative Scale Applications of C−H Activation in Medicinal Chemistry DOI Creative Commons
Rita de Jesus, Kerstin Hiesinger, Manuel van Gemmeren

и другие.

Angewandte Chemie International Edition, Год журнала: 2023, Номер 62(45)

Опубликована: Июнь 7, 2023

C-H activation is an attractive methodology to increase molecular complexity without requiring substrate prefunctionalization. In contrast well-established cross-coupling methods, less explored on large scales and its use in the production of pharmaceuticals faces substantial hurdles. However, inherent advantages, such as shorter synthetic routes simpler starting materials, motivate medicinal chemists process overcome these challenges, exploit steps for synthesis pharmaceutically relevant compounds. this review, we will cover examples drugs/drug candidates where has been implemented a preparative scale (range between 355 mg 130 kg). The optimization processes be described, each example examined terms advantages disadvantages, providing reader with in-depth understanding challenges potential methodologies pharmaceuticals.

Язык: Английский

Процитировано

33
Control of Selectivity in Homogeneous Catalysis through Noncovalent Interactions DOI Creative Commons
Kamran T. Mahmudov⧫, Armando J. L. Pombeiro

Chemistry - A European Journal, Год журнала: 2023, Номер 29(26)

Опубликована: Фев. 23, 2023

The regio-, site-, stereo- or chemoselective homogeneous catalytic transformations are extremely important for the growth/success of current chemical industry. Based on empirical, theoretical intuitive knowledge, several synthetic strategies, such as ligand design, transient directing group, metal node alternation, metal-ligand cooperation, pore decoration, biomimetic, have already been developed selective functionalization organic substrates. In comparison to other tactics, use noncovalent interactions control selectivity in compounds may avoid multi-steps, reduce time procedure, decrease cost operation, and increase reactivity catalyst. fact, enzymes achieve a high through biochemical processes Nature. Guided by impressive performance biosynthesis biodegradation reactions, various types complex organocatalysts developed, which catalyst-substrate pivotal impact distinctive stabilization transition states intermediates, improving efficiency reactions. Herein, we highlight recent relevant examples directing/driving function transformation substrate(s) catalyzed both catalysts.

Язык: Английский

Процитировано

31
Carbonylative Formal Cycloaddition between Alkylarenes and Aldimines Enabled by Palladium-Catalyzed Double C–H Bond Activation DOI
Yongzheng Ding, Jianing Wu, Hanmin Huang

и другие.

Journal of the American Chemical Society, Год журнала: 2023, Номер 145(9), С. 4982 - 4988

Опубликована: Фев. 23, 2023

Double C-H bond activation can enable an expeditious reaction pathway to cyclic compounds, offering efficient tool synthesize valuable molecules. However, cyclization enabled by double at one carbon atom is nearly unknown. Herein, we report a carbonylative formal cycloaddition of alkylarenes with imines via benzylic atom, allowing straightforward synthesis β-lactams from readily accessible and imines, which paves the way for developing annulation through atom.

Язык: Английский

Процитировано

31