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

Synfacts, Год журнала: 2023, Номер 19(11), С. 1114 - 1114

Опубликована: Окт. 14, 2023

Key words palladium catalysis - C–H functionalization spirocycles

Язык: Английский

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

Qianting Zhou,

Bin Li, Xinying Zhang

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(12), С. 2324 - 2338

Опубликована: Янв. 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.

Язык: Английский

Процитировано

22

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

Sagarika Patra,

Rojalini Maharana

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(15), С. 2916 - 2947

Опубликована: Янв. 1, 2024

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

Язык: Английский

Процитировано

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

и другие.

Organic Letters, Год журнала: 2024, Номер 26(7), С. 1338 - 1342

Опубликована: Фев. 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.

Язык: Английский

Процитировано

6

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

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(19), С. 4139 - 4144

Опубликована: Июль 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.

Язык: Английский

Процитировано

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

и другие.

Angewandte Chemie International Edition, Год журнала: 2024, Номер 63(45)

Опубликована: Июль 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).

Язык: Английский

Процитировано

3

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, Год журнала: 2025, Номер unknown

Опубликована: Фев. 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.

Язык: Английский

Процитировано

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, Год журнала: 2025, Номер unknown

Опубликована: Апрель 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.

Язык: Английский

Процитировано

0

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

E. Premkumar,

Ramdas Sreedharan,

Premananda Ghosh

и другие.

Chemical Society Reviews, Год журнала: 2025, Номер unknown

Опубликована: Янв. 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.

Язык: Английский

Процитировано

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

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер unknown

Опубликована: Март 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.

Язык: Английский

Процитировано

1

Synthesis of Aza‐Bicyclic Maleimide Skeleton by Addition‐Ring Opening Cascade Reaction of Vinylogous Oxindole DOI
Qian Liao, Yang Zhang, Jin‐Yu Liu

и другие.

European Journal of Organic Chemistry, Год журнала: 2024, Номер 27(20)

Опубликована: Апрель 1, 2024

Abstract An efficient method has been developed to facilitate the addition‐ring opening cascade reaction of vinylogous oxindole, resulting in synthesis a variety aza‐bicyclic maleimide derivatives with high yields and exceptional diastereoselectivities. Furthermore, product could be effectively easily transformed into difluoromethylenecyclohexane skeleton through dehydrofluorination process. This methodology demonstrates significant potential for skeleton, which possesses biological or pharmaceutical activity.

Язык: Английский

Процитировано

1