Synthesis of CF3-Substituted N-Heterocyclic Compounds Based on C–H Activation-Initiated Formal [2 + 3] Annulation Featuring with a Latent Nucleophilic Site DOI

Manqing Wang,

Shengnan Yan,

Bin Li

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(11), P. 7828 - 7842

Published: May 22, 2024

Presented herein is a novel synthesis of CF

Language: Английский

Design principles of the use of alkynes in radical cascades DOI
Chaowei Hu,

Justice Mena,

Igor V. Alabugin

et al.

Nature Reviews Chemistry, Journal Year: 2023, Volume and Issue: 7(6), P. 405 - 423

Published: March 28, 2023

Language: Английский

Citations

53

C–H activation-initiated spiroannulation reactions and their applications in the synthesis of spirocyclic compounds DOI

Qianting Zhou,

Bin Li, Xinying Zhang

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(12), P. 2324 - 2338

Published: Jan. 1, 2024

This review summarizes the most recent progress made in C–H bond activation-initiated spiroannulation reactions and their applications construction of structurally diverse biologically valuable spirocyclic scaffolds.

Language: Английский

Citations

22

Synthesis of Benzoisochromene Derivatives via C–H Activation-Initiated Cascade Formal [4+2] and [2+4] Annulation of Aryl Enaminone with Vinyl-1,3-dioxolan-2-one DOI

Chun Xia Yang,

Bin Li, Peng Shi

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: March 19, 2025

Cascade annulation reactions can assemble structurally intricate polycyclic molecules from simple starting materials with enhanced efficiency and minimized production of waste. Presented herein is a concise effective synthesis benzoisochromene derivatives based on C-H activation-initiated cascade formal [4+2]/[2+4] aryl enaminone vinyl-1,3-dioxolan-2-one. In constructing the six-membered carbocycle, acted as C4 synthon while vinyl-1,3-dioxolan-2-one C2 synthon. O-heterocycle, other hand, former latter C3O1 To our knowledge, this first simultaneous construction both carbocycle an O-heterocycle via concurrent C-H/C-N/C-O bond cleavage C-C/C-C/C-O formation. general, novel protocol features use readily obtainable substrates broad scope, excellent atom- step-economy, intriguing reaction pathway, valuable products.

Language: Английский

Citations

3

Rhodium‐Catalyzed Atroposelective Access to Axially Chiral Olefins via C−H Bond Activation and Directing Group Migration DOI

Ruijie Mi,

Haohua Chen, Xukai Zhou

et al.

Angewandte Chemie International Edition, Journal Year: 2021, Volume and Issue: 61(1)

Published: Oct. 22, 2021

Axially chiral open-chain olefins represent an underexplored class of platform. In this report, two classes tetrasubstituted axially acyclic have been accessed in excellent enantioselectivity and regioselectivity via C-H activation (hetero)arenes assisted by a migratable directing group en route to coupling with sterically hindered alkynes. The indoles bearing N-aminocarbonyl afforded C-N acrylamides the assistance racemic zinc carboxylate additive. DFT studies suggest β-nitrogen elimination-reinsertion pathway for migration. Meanwhile, employment N-phenoxycarboxamide delivered C-C enamides migration oxidizing group. Experiments that both cases (hetero)arene substrate adopts well-defined orientation during activation, which turn determines disposition alkyne migratory insertion. Synthetic applications representative are demonstrated.

Language: Английский

Citations

97

C–H bond functionalization by high-valent cobalt catalysis: current progress, challenges and future perspectives DOI
Lukass Lukasevics, Aleksandrs Cizikovs, Liene Grigorjeva

et al.

Chemical Communications, Journal Year: 2021, Volume and Issue: 57(83), P. 10827 - 10841

Published: Jan. 1, 2021

Over the last decade, high-valent cobalt catalysis has earned a place in spotlight as valuable tool for C-H activation and functionalization. Since discovery of its unique reactivity, more attention been directed towards utilization an alternative to noble metal catalysts. In particular, Cp*Co(III) complexes, well simple Co(II) Co(III) salts combination with bidentate chelation assistance, have extensively used development novel transformations. this review, we demonstrated existing trends functionalization methodology using highlighted main challenges overcome, perspective directions, which need be further developed future.

Language: Английский

Citations

69

Divergent C(sp2)–H arylation of heterocycles via organic photoredox catalysis DOI
Jie Ren, Chao Pi, Xiuling Cui

et al.

Green Chemistry, Journal Year: 2022, Volume and Issue: 24(7), P. 3017 - 3022

Published: Jan. 1, 2022

Introducing aryl moieties into heterocyclic scaffolds is a key step in the syntheses of natural products, drugs, and functional materials.

Language: Английский

Citations

49

Tandem Reactions involving 1,4‐Palladium Migrations DOI
Mengyao Li, Dong Wei, Chen‐Guo Feng

et al.

Chemistry - An Asian Journal, Journal Year: 2022, Volume and Issue: 17(15)

Published: June 6, 2022

Abstract Transition‐metal‐catalyzed tandem reactions have become a mainstay in organic chemistry owing to their high atom‐ and step‐economies. Metal‐migration‐based allow the engagement of simple starting materials for incorporating functional groups into certain positions constructing complex scaffolds, which provide novel means that are complementary traditional cross‐coupling or C−H activation processes. In light broad utility 1,4‐Pd migration reaction, this paper reviews its progress past two decades, summarizing process classifying it based on insertion, elimination, transmetalation, bond activation. Special emphasis is placed driving force Pd different mechanisms. Moreover, review also attempts summarize common strategies improving regio‐ site‐selectivities process.

Language: Английский

Citations

44

Recent Advances in Transition-Metal-Catalyzed C–H Alkylation with Three-Membered Rings DOI

Huihong Wang,

Xiaodong Wang,

Gaofeng Yin

et al.

ACS Catalysis, Journal Year: 2022, Volume and Issue: 12(4), P. 2330 - 2347

Published: Feb. 1, 2022

Transition-metal-catalyzed alkylation of (hetero)arenes with three-membered carbo-/heterocycles involving C–H activation and ring scission has been greatly developed over the past few years. The chelation-assisted strategies for controlling reactivity site selectivity in these protocols include use nitrogen-containing directing groups, pre-existing functional a Catellani-type intermediate, thereby providing rapid access to numerous oxygen- or heterocyclic systems. This review gives an update area various catalytic methodologies applications total synthesis natural products rings as alkylating reagents, which are classified into following three categories on basis employed strategies: (i) directed by (ii) (iii) aryl-NBE intermediates (Catellani-type cascade reaction).

Language: Английский

Citations

40

Condition-Controlled Selective Synthesis of Pyranone-Tethered Indazoles or Carbazoles through the Cascade Reactions of N-Nitrosoanilines with Iodonium Ylides DOI
Kelin Wang,

Xia Song,

Yongdi Xin

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(24), P. 4422 - 4428

Published: June 8, 2023

Presented herein is a condition-controlled selective synthesis of pyranone-tethered indazoles or carbazole derivatives via the cascade reactions N-nitrosoanilines with iodonium ylides. Mechanistically, formation former involves an unprecedented process including nitroso group-directed C(sp2)–H bond alkylation N-nitrosoaniline ylide followed by intramolecular C-nucleophilic addition to moiety, solvent-assisted cyclohexanedione ring opening, and transesterification/annulation. On contrary, latter initial annulation denitrosation. These developed protocols feature easily controllable selectivity, mild reaction conditions, clean sustainable oxidant (air), valuable products that are structurally diverse. In addition, utility was showcased their facile diverse transformations into synthetically biologically interesting compounds.

Language: Английский

Citations

27

Synthesis of functionalized quinolines from the cascade reactions of N-aryl amidines with two CF3-ynones via C–H/N–H/C–N/C–C bond cleavage DOI
Hao Li,

Shengnan Yan,

Yuanshuang Xu

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(7), P. 1917 - 1923

Published: Jan. 1, 2024

We present a novel synthesis of CF 3 - and alkynyl-substituted quinoline derivatives based on Rh( iii )-catalyzed cascade reactions N -aryl amidines with two -ynones. Then, some products are transformed into polycyclic -benzo[ k ]phenanthridines through an intramolecular annulation reaction.

Language: Английский

Citations

14