Pd(II)-Catalyzed C(sp3)–H Activation/Spirocyclization of Alkyl Amides DOI
Mark Lautens, Alexa Torelli

Synfacts, Journal Year: 2023, Volume and Issue: 19(11), P. 1114 - 1114

Published: Oct. 14, 2023

Key words palladium catalysis - C–H functionalization spirocycles

Language: Английский

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
Recent advances in spirocyclization of maleimides via transition-metal catalyzed C–H activation DOI
Swadhin Swaraj Acharya,

Sagarika Patra,

Rojalini Maharana

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(15), P. 2916 - 2947

Published: Jan. 1, 2024

In recent years, the maleimide scaffold has received a great deal of attention in C–H activation.

Language: Английский

Citations

15
Palladium-Catalyzed (3 + 2) Annulation of Aromatic Acids by C(sp3)–H Olefination and Decarboxylative Cross-Coupling Reaction DOI
Xiaobo Xu, Yangyang Wang, Xiao Yu

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(7), P. 1338 - 1342

Published: Feb. 9, 2024

A palladium-catalyzed (3 + 2) annulation of 2-methylbenzoic acid with maleimide using Ac-Leu-OH as a powerful ligand has been reported. Through site-selective γ-C(sp3)–H olefination reaction and sequential decarboxylative cross-coupling reaction, five-membered cyclic ring was obtained the final product. This novel features great site selectivity reactivity to generate various products in moderate good yields.

Language: Английский

Citations

6
Synthesis of γ-Lactams via Palladium-Catalyzed C(sp3)–H Bond Activation of Alkyl Sulfonamides with Substituted Alkenes DOI
Ananya Dutta, Masilamani Jeganmohan

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

Published: Feb. 20, 2025

A methodology for the γ-butyrolactam scaffolds via ligand-enabled C(sp3)–H bond functionalization of sulfonamides with olefins has been demonstrated. The protocol found to be compatible several activated and unactivated olefins, desired lactams were formed in excellent yields. plausible mechanism described account lactamization reaction as well supported by mechanistic investigation including a 1H NMR study isolation palladacycle intermediate.

Language: Английский

Citations

0
Palladium-Catalysed Spiro-Cyclisation of Substituted Amino Acids with Maleimides via γ-C(sp3)–H Bond Activation DOI

Trisha Chakraborty,

Masilamani Jeganmohan

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

Published: April 1, 2025

Achieving the site-selective functionalization of unactivated C(sp3)-H bonds remains a major challenge in organic synthesis. Herein, we report an efficient method for synthesis spiro pyrrolidine molecules via γ-C(sp3)-H bond activation substituted amino acids. A variety acid and alcohol derivatives, as well dipeptides, were functionalized using this method. Also, spirocyclization optically active substrates provided potential route preparing separable diastereomers pure enantiomeric form. Moreover, some mechanistic insights have been conducted to propose feasible reaction mechanism present reaction.

Language: Английский

Citations

0
Copper(II)‐Catalyzed [2+2+2] Annulation of Enaminones with Maleimides Using a Traceless Directing Group Strategy DOI
Leiqing Fu, Hongxiang Huang, Yingying Jiang

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(19), P. 4139 - 4144

Published: July 2, 2024

Abstract A copper‐catalyzed annulation of enaminones with maleimides was developed to synthesize various pyrrolo[3,4‐e]isoindoles. In this strategy, 2‐aminopyridine served as a traceless directing group, and target products were obtained in 54–72% yields. Moreover, plausible mechanism for reaction proposed based on several control experiments, deuterium exchange previous reports.

Language: Английский

Citations

3
Ligand‐Enabled Pd‐Catalyzed sp3 C−H Macrocyclization: Synthesis and Evaluation of Macrocyclic Sulfonamide for the Treatment of Parkinson's Disease DOI Open Access

Tongyu Bi,

Yunxia Cui, Shuai Liu

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(45)

Published: July 30, 2024

Abstract The development of simplified synthetic strategy to create structurally and functionally diverse pseudo‐natural macrocyclic molecules is highly appealing but poses a marked challenge. Inspired by natural scaffolds, herein, we describe practical concise ligand‐enabled Pd(II)‐catalyzed sp 3 C−H alkylation, olefination arylation macrocyclization, which could offer novel set sulfonamides. Interestingly, the potential ligand acceleration in activation also demonstrated an unprecedented enantioselective alkylation macrocyclization. Moreover, combination silico screening biological evaluation led identification spiro‐grafted sulfonamide 2 , showed promising efficacy for treatment Parkinson's disease (PD) mouse model through silent information regulator sirtuin (SIRT3).

Language: Английский

Citations

3
Synthesis of lactones and lactams via C(sp3)–H bond functionalization DOI

E. Premkumar,

Ramdas Sreedharan,

Premananda Ghosh

et al.

Chemical Society Reviews, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

In this review, we have showcased the diverse aspects of transition-metal catalysis, biocatalysis, and photocatalytic C(sp 3 )–H bond functionalization to access lactones lactams.

Language: Английский

Citations

0
Chemoselective Oxypalladation of (o‐Alkynylaryl)amide‐Triggered Site‐Selective C−H Annulation for Stereoselective Synthesis of Succinimide‐Fused Polycycles DOI

Dattatri,

Jagadeesh Babu Nanubolu, Maddi Sridhar Reddy

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: unknown

Published: March 20, 2024

Abstract We report herein a palladium‐catalyzed, site‐selective cyclative annulation of o ‐alkynyl arylamides with maleimide for the stereoselective construction succinimide‐fused benzoxazine derivatives. This operationally simple and modular protocol provides access to polycyclic frameworks. The other associated features are high functional group compatibility, gram‐scale synthetic potential, downstream transformations. Control labeling experiments were conducted get insights into mechanism.

Language: Английский

Citations

1
Maleimide-Dependent Rh(III)-Catalyzed Site-Selective Mono and Dual C–H Functionalization of 2-Arylbenzo[d]thiazole and Oxazole Derivatives DOI

Vidya Kumari,

Swadhin Swaraj Acharya,

Nurabul Mondal

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 3, 2024

The site-selective functionalization of aromatic compounds via C–H activation has emerged as a popular tool in organic synthesis. In this study, we report regioselective coupling maleimide to 2-arylbenzo[d]thiazoles the presence rhodium(III) catalyst. Depending upon nature substituent (R2-group) present substrate, either mono- or bis-1,4-addition products were observed methodology. case R2 = aryl, cyclohexyl, and tert-butyl, mono was observed, whereas substituents, such methyl, ethyl, benzyl, methyl thiophene, provided bis major products. Similar selectivity also 2-arylbenzo[d]oxazoles.

Language: Английский

Citations

1