Construction of Covalent Triazine Frameworks with Electronic Donor‐Acceptor System for Efficient Photocatalytic C−H Hydroxylation of Imidazole[1,2‐α]Pyridine Derivatives DOI
Lipeng Zhai, Huijie Qiao,

Zhao Kun

et al.

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(61)

Published: Aug. 15, 2024

Abstract Covalent triazine frameworks (CTFs) are promising heterogeneous photocatalyst candidates owing to their excellent stability, conjugacy, and tunability. In this study, a series of CTFs decorated with different substituents (H, MeO, F) were synthesised utilised as photocatalysts for C−H activation reactions. The corresponding optoelectronic properties could be precisely regulated by the electronic effects in nanopore channels CTFs; these effective organic synthesis due unique structures properties. Methoxy‐substituted CTF (MeO‐CTF) exhibited extraordinary catalytic performance reusability functionalization constructing an donor‐acceptor system, achieving highest yield photocatalytic C3–H hydroxylation 2‐phenylimidazole[1,2‐α]pyridine. This strategy provides new scaffold rational design efficient synthesis.

Language: Английский

Rh(III)‐Catalyzed Direct ortho Alkylation of Carbazoles with Nitroalkenes DOI Open Access
Liming Zhang,

Ru Zhao,

Chunhui Liu

et al.

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(20), P. 3461 - 3466

Published: Aug. 26, 2023

Abstract The Rh(III)‐catalyzed ortho alkylation of N ‐pyridylcarbazoles with nitroalkenes has been developed, furnishing a wide range 2‐(2‐nitroalkyl)carbazoles. Both aromatic and aliphatic participated in this reaction successfully. This protocol also proceeded well an indoline based substrate. Derivatization the representative nitroalkane product was described.

Language: Английский

Citations

8
A general photochemical strategy for the oximation of activated alkenes without a catalyst DOI

Hongyan Lan,

You Su,

Y. Chen

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(15), P. 4207 - 4213

Published: Jan. 1, 2024

A general photochemical approach for the oximation of activated alkenes to synthesize diverse oximes without catalysts is described. The simple and modular method offers a new perspective chemists rapidly obtain various radical intermediates.

Language: Английский

Citations

3
Palladium-Catalyzed Selective Benzylic C–H Alkylation of Aromatic Sulfonamides with Maleimides DOI

Trisha Chakraborty,

Gouranga Naskar,

Masilamani Jeganmohan

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(15), P. 10624 - 10638

Published: July 12, 2024

An efficient method for the selective benzylic C-H alkylation of sulfonamides using maleimides has been developed. The reaction proceeds

Language: Английский

Citations

3
Unlocking C–H Functionalization at Room Temperature via a Light-Mediated Protodemetalation Reaction DOI
Claire Empel, Sripati Jana,

Adithyaraj Koodan

et al.

ACS Catalysis, Journal Year: 2022, Volume and Issue: 12(14), P. 8229 - 8236

Published: June 26, 2022

Herein, we report on the photocatalytic ortho-alkylation reaction of 2-phenyl pyridines with N-protected maleimides using [Cp*RhCl2]2 as a catalyst and propionic acid an additive at room temperature. Experimental theoretical studies suggest mechanism that consists dark light reaction: while cyclometalation migratory insertion can proceed temperature in dark, photochemical excitation intermediates is required to facilitate decomplexation directing group allow ligand exchange acid. This enables facile protodemetalation regenerate give product. We studied this broad substrate scope, including different groups N-substituted yield succinimides high (49 examples, up 96% yield).

Language: Английский

Citations

13
Synthesis of Succinimide-Linked Indazol-3-ols Derived from Maleimides under Rh(III) Catalysis DOI Creative Commons

Ju Young Kang,

Suho Kim,

Junghyea Moon

et al.

ACS Omega, Journal Year: 2022, Volume and Issue: 7(17), P. 14712 - 14722

Published: April 21, 2022

The structural modification of N-aryl indazolols as tautomers indazolones has been established a hot topic in pharmaceutics and medicinal chemistry. We herein disclose the rhodium(III)-catalyzed 1,4-addition reaction maleimides with indazol-3-ols, which provides succinimide-bearing indazol-3-ol scaffolds complete regioselectivity good functional group tolerance. Notably, versatility this protocol is demonstrated by use drug-molecule-linked fluorescence-probe-linked maleimides.

Language: Английский

Citations

12
One-Step Syntheses of 3,4-Disubstituted Isochroman-1-ones by the Annulation of Benzoic Acids with Nitroalkenes DOI
Shuang‐Liang Liu,

Xulin Lv,

Xiaoge Wang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(5), P. 3672 - 3676

Published: Feb. 21, 2024

The Rh(III)-catalyzed annulation of benzoic acids with nitroalkenes was disclosed to afford a wide range 3,4-disubstituted isochroman-1-ones excellent regioselectivity and high catalytic efficiency. Both aromatic aliphatic participated in this cyclization reaction successfully. synthetic value proven by series derivatizations. Furthermore, reliable mechanism is outlined on the basis experimental investigations related precedents.

Language: Английский

Citations

2
Catalytic Enantioselective Functionalization of Maleimides: An Update DOI Creative Commons
Muriel Amatore, Damien Bonne,

Thierry Constantieux

et al.

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: 42(24), P. 3605 - 3622

Published: Nov. 13, 2024

Comprehensive Summary Maleimide derivatives are well‐established reactive intermediates also found in natural products, synthetic pharmaceuticals and functional polymers. Their specific reactivity widespread applications the field of bioconjugation allowed for development highly selective functionalizations based on simple additions cycloadditions with possible control central C–N axial chirality. These multisite‐reactive scaffolds have aroused a long‐standing interest throughout scientific community more particularly as powerful electrophilic partners recently nucleophilic some transformations. The persistent these easily accessible platforms over last decade has enabled new enantioselective transformations major advancements this presented review. Key Scientists

Language: Английский

Citations

2
Selective Construction of Spiro or Fused Heterocyclic Scaffolds via One-pot Cascade Reactions of 1-Arylpyrazolidinones with Maleimides DOI
Na Li,

Bing Hu,

Xinying Zhang

et al.

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 88(1), P. 60 - 74

Published: Dec. 23, 2022

Presented herein is a controllable selective construction of spiro or fused heterocyclic scaffolds through the one-pot cascade reactions 1-phenylpyrazolidinones with maleimides. To be specific, succinimide pyrazolo[1,2-a]pyrazolones were effectively formed via [4 + 1] spiroannulation maleimides simultaneous C(sp2)-H bond activation/functionalization and intramolecular cyclization along traceless fusion pyrazolidinonyl unit into final product. In this reaction, air acts as cost-effective environmentally sustainable oxidant to assist regeneration Rh(III) catalyst. Alternatively, succinimide-fused pyrazolidinonylcinnolines from same starting materials an initial followed by base-promoted skeleton rearrangement in situ product without isolation. Notable features these protocols include easily tunable selectivity, broad substrate scope, oxidant, excellent atom economy, facile scalability.

Language: Английский

Citations

11
Rhodium(iii)-catalysed redox neutral alkylation of 3-arylbenzo[d]isoxazoles: easy access to substituted succinimides DOI

Xuelin Yue,

Xiang Zhao,

Junwei Huang

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(29), P. 5985 - 5989

Published: Jan. 1, 2023

A convenient method for the alkylation of 3-arylbenzo[d]isoxazoles with maleimides under redox-neutral conditions has been developed, giving a series substituted succinimides in up to 99% yield. This transformation is highly selective give succinimides, and Heck-type products are successfully avoided. protocol features 100% atom-economy broad substrate tolerance, provides novel strategy synthesis diverse an opportunity succinylation protein medication pharmacologists discover first-in-class drugs.

Language: Английский

Citations

6
Rh(III)‐Catalyzed C−H Activation/O‐Annulation for Construction of Divergent Spirosuccinimide and Maleimide‐Fused Isochromenes DOI
Eswaran Kamaraj,

Prasanta Roy,

Yong Rok Lee

et al.

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(22), P. 3915 - 3926

Published: Sept. 12, 2023

Abstract A rhodium‐catalyzed [5+1] cycloaddition via C−H activation/ O ‐annulation strategy for synthesizing biologically interesting isochromenes is presented. This protocol selectively provides divergently functionalized containing spirosuccinimide and maleimide scaffolds according to the maleimides itaconimides used as substrates. methodology exhibits an extensive substrate scope, remarkable functional group tolerance, high regioselectivity.

Language: Английский

Citations

6