Synthesis of 3‐Arylacetamides Substituted Maleimide Via Weakly Coordinating Acetamide Assisted Cross‐dehydrogenative Coupling and Their Photophysical Studies DOI
Saksham Mishra, Amit Kumar

European Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 2022(44)

Published: Oct. 21, 2022

Abstract Maleimides serve as an important synthetic precursor for various organic transformation reactions. However, maleimides have been rarely employed coupling partners the direct synthesis of 3‐aryl substituted via oxidative Heck‐type reaction, due to lack β‐hydrogen at syn‐periplanar position. Therefore, herein, we report efficient and highly selective 3‐arylacetamide incorporated through cross‐dehydrogenative process using simple native primary acetamide a weakly directing group with Pd(II)‐catalysis conditions. This reaction furnishes 3‐arylated maleimide derivatives in good yields high functional tolerance. Furthermore, were transformed into synthetically derivatives. Based on preliminary control experiments, probable mechanism has proposed distal C−H bond functionalization reaction. Interesting photophysical properties synthesized products also observed.

Language: Английский

Recent advances in transition-metal-catalyzed directed C–H alkenylation with maleimides DOI
Shuang‐Liang Liu, Changchun Ye, Xiaoge Wang

et al.

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 20(24), P. 4837 - 4845

Published: Jan. 1, 2022

Transition-metal-catalyzed directed C-H alkenylation with maleimides has attracted much attention in recent years, as maleimide core moieties are present various natural products and pharmaceuticals. In addition, these derivatives can be readily modified into biologically important compounds including succinimides, pyrrolidines γ-lactams. The efficient chelation-assisted inert bond activation strategy provides straightforward access to a wide array of structurally diverse molecules containing units. This review describes the major progress mechanistic investigations on Heck-type reaction/cyclization organic until early 2022.

Language: Английский

Citations

32
Preparation of reusable copper-based biomass-carbon aerogel catalysts and their application in highly selective reduction of maleimides to succinimides with hydrosilane as a hydrogen source DOI

Shaohuan Lv,

Zhanhong Yuan,

Juanjuan Zheng

et al.

Green Chemistry, Journal Year: 2024, Volume and Issue: 26(5), P. 2592 - 2598

Published: Jan. 1, 2024

A novel copper-based biomass-carbon aerogel catalyst was prepared as a highly efficient and selective for maleimides reduction the first time with excellent catalytic activity, chemo-selectivity, recyclability.

Language: Английский

Citations

5
Macrocyclization of Maleimide-Decorated Peptides via Late-Stage Rh(III)-Catalyzed Trp(C7) Alkenylation DOI
Yu Zhang,

Shulei Hu,

Yazhou Li

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(14), P. 2456 - 2460

Published: March 31, 2023

Here, we report a novel strategy for constructing maleimide-containing peptides and cyclic using Rh(III)-catalyzed tryptophan (Trp) (C7) alkenylation, which is challenging due to the inherent reactivity of indole benzenoid ring. This method scalable exhibits broad substrate scope. The utility this protocol could further be demonstrated by synthesis peptide conjugates with natural products amino acids as well construction maleimide-braced peptides.

Language: Английский

Citations

11
Redox‐Neutral Synthesis of Polycyclic Azaheterocycles via Cobalt‐Catalyzed Hydroarylation/Annulation of Maleimides DOI

Yequan He,

Wen‐Wei Li,

Honggui Zhou

et al.

Advanced Synthesis & Catalysis, Journal Year: 2022, Volume and Issue: 364(21), P. 3730 - 3735

Published: Sept. 15, 2022

Abstract Herein, we report a cobalt‐catalyzed hydroarylation of maleimides followed by an annulation sequence for the synthesis polycyclic azaheterocycles in one pot. The reaction proceeds under redox‐neutral conditions and is compatible with various functional groups. Notably, as‐prepared product exhibits potential photophysical properties. magnified image

Language: Английский

Citations

17
Design and Synthesis of 7-(N-Aryl Pyrrolidinyl) Indoles as Potential DCAF15 Binders DOI Creative Commons
Ravi Devarajappa,

Scarlett Kiyeleko,

Sofiane Hocine

et al.

Reactions, Journal Year: 2025, Volume and Issue: 6(1), P. 20 - 20

Published: March 7, 2025

We describe the design and synthesis of a series 7-(N-aryl pyrrolidinyl) indoles oxo-analogs as isosteric mimics DCAF15 binder E7820, well-known member aryl sulfonamides known SPLAMs. The functionalization C-7 in was achieved by metal-catalyzed CH-activation with unexpected results. Binding assays revealed pyrrolidine N-aryl carboxylic acid analog to be equally active E7820.

Language: Английский

Citations

0
Rhodium‐Catalyzed C8‐Alkenylation of Isoquinolones with Maleimides DOI

XXXXXXX Manisha,

Devesh Chandra, Upendra Sharma

et al.

European Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 26(30)

Published: June 15, 2023

Abstract An efficient Rh(III)‐catalyzed C−H alkenylation of N ‐protected isoquinolone with maleimides is reported. The carbonyl group acts as an inherent directing group. Various ‐substituents in the maleimide, including alkyl, aryl, and even H −OH, were well tolerated under developed reaction condition. This protocol showed broad substrate scope, good selectivity, excellent yields. Hammett plot also drawn to check effect substituents on progress.

Language: Английский

Citations

9
Regioselective peri-C–H selenylation of aromatic compounds with weakly coordinating ketone groups DOI
Bingbing Duan, Yao Wu, Yi Gao

et al.

Chemical Communications, Journal Year: 2022, Volume and Issue: 58(82), P. 11555 - 11558

Published: Jan. 1, 2022

A novel and versatile method for peri-C-H selenylation of aromatic compounds bearing ketone groups, including chromones, xanthones, acridinones, quinolinones naphthoquinones with diselenides under Ru(II) catalysis is presented. Various chromones are applicable this transformation, affording 5-selenyl in a highly regioselective manner good to excellent yields. This transformation easy scale up the desired products can be further modified. Most importantly, allows late-stage bioactive compounds. Mechanistic studies show that radicals may involved transformation.

Language: Английский

Citations

11
Rhodium-Catalyzed Regioselective C3Ar Functionalization of Tyrosines with Maleimides and Its Late-Stage Peptide Exemplification DOI

Narendra Dinkar Kharat,

Sushma Naharwal,

Disha Tank

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(42), P. 7673 - 7677

Published: Oct. 19, 2023

Pyridyloxy-directed Rh(III)-catalyzed regioselective C3Ar-H alkenylation of protected tyrosines was achieved with N-aryl and N-alkyl maleimides, furnishing a series maleimide-appended tyrosine-based unnatural amino acids in good yields. Further, the late-stage exemplification strategy successfully accomplished on tyrosine-containing dipeptides, tripeptides, tetrapeptides moderate reactivity. Also, chemical applications were executed toward nailing tyrosine other via maleimide linker intramolecular hydroarylation to produce tyrosine-centered stapled products succinimide-glued macrocyclized products, respectively.

Language: Английский

Citations

4
Rh(III)-catalyzed late-stage C-H alkenylation and macrolactamization for the synthesis of cyclic peptides with unique Trp(C7)-alkene crosslinks DOI

Shulei Hu,

Yu Zhang,

Xiong Xie

et al.

Chinese Chemical Letters, Journal Year: 2023, Volume and Issue: 35(8), P. 109408 - 109408

Published: Dec. 19, 2023

Language: Английский

Citations

4
Recent Progress on Transition Metal Catalyzed Macrocyclizations Based on C‐H Bond Activation at Heterocyclic Scaffolds DOI

Sarbojit Das,

Tapan Kumar Pradhan, Rajarshi Samanta

et al.

Chemistry - An Asian Journal, Journal Year: 2024, Volume and Issue: unknown

Published: June 24, 2024

Abstract Macrocycles are essential in protein‐protein interactions and the preferential intake of bioactive scaffolds. commonly synthesized by late‐stage macrolactonizations, macrolactamizations, transition metal‐catalyzed ring‐closing metathesis, S−S bond‐forming reactions, copper‐catalyzed alkyne–azide cycloaddition. Recently, C−H activation strategies have gained significant interest among chemists to synthesize macrocycles. This article provides a comprehensive overview macrocyclization via bond functionalization heterocycle‐containing peptides, annulations, heterocycle‐ring construction through direct functionalization. In first part, palladium salt catalyzed coupling with indolyl C(sp 3 )−H 2 bonds for is reported. The second part summarizes rhodium‐catalyzed macrocyclizations site‐selective Earth‐abundant, less toxic 3d metal Mn‐catalyzed cyclizations reported latter part. summary expected spark emerging methods macrocycle production organic synthesis chemical biology practitioners, helping develop discipline. We hope that this mini‐review will also inspire synthetic explore new broadly applicable C−C intramolecular activation.

Language: Английский

Citations

1