Palladium-Catalyzed Enantioselective Intramolecular Heck Dearomative Annulation of Indoles with N-Tosylhydrazones DOI Open Access
Yue Ma, Congcong Lu,

Sheng-Qi Xu

и другие.

Authorea (Authorea), Год журнала: 2024, Номер unknown

Опубликована: Янв. 30, 2024

An elegant Pd(dba)2-catalyzed enantioselective Heck dearomative annulation of indoles and N-tosylhydrazones for the straightforward assembly structurally diverse optically active indoline scaffolds containing quaternary carbon centers at C2-position has been developed. The tandem protocol, which utilized Pd(dba)2/BINOL-based phosphoramidite ligand as catalytic system, proceeded smoothly through successive oxidative addition, intramolecular palladation, migratory insertion, reductive elimination se-quences, leading to chiral derivatives in moderate excellent yields, with enantioselectivities diastereoselec-tivities. In synthetic practicability system was underlined by a scaled-up experiment late-stage derivatization products, thus highlighting potential applications chemistry, medicinal material science.

Язык: Английский

Palladium-Catalyzed Intramolecular Heck Dearomative Alkenylation of Indoles with N-Tosylhydrazones DOI

Shao-Bo Duan,

Hong‐Yu Zhang, Yue Ma

и другие.

The Journal of Organic Chemistry, Год журнала: 2022, Номер 87(16), С. 10917 - 10927

Опубликована: Авг. 10, 2022

An elegant Pd-catalyzed intramolecular Heck dearomative alkenylation of aryl iodides with functionalized N-tosylhydrazones proceeded through a sequential carbopalladation, migratory insertion, and β-hydride elimination in the presence Pd(CF3COO)2 (10 mol %), PPh3 (30 Cs2CO3 (2.0 equiv) 1,4-dioxane mL) at 120 °C for 14 h under an argon atmosphere. This cascade cycloaddition protocol provided reliable versatile approach to sequence structurally diverse indolines moderate good yields functional group compatibility. In addition, synthetic robustness methodology is highlighted by scaled-up experiment derivatization products via epoxidation reduction reactions.

Язык: Английский

Процитировано

6

Palladium-catalyzed cascade cyclization/intramolecular redox-relay Heck arylation of alkenols: access to tetrahydro-β-carbolines from 2-(hydroxyalkenynyl)sulfonanilides DOI
Tao Liu, Tuanli Yao, Ruihua Guo

и другие.

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(14), С. 3504 - 3508

Опубликована: Янв. 1, 2023

The first palladium-catalyzed cascade reaction combining Pd( ii )-catalyzed nucleophilic cyclization of alkynes and intramolecular redox-relay Heck arylation alkenols has been developed.

Язык: Английский

Процитировано

3

Synthesis of Chiral Heterocycles from Asymmetric Cascade Palladium Catalysis DOI

Hélène Pellissier

Current Organic Chemistry, Год журнала: 2023, Номер 27(2), С. 71 - 92

Опубликована: Янв. 1, 2023

Abstract: This review updates the field of asymmetric cascade palladium catalysis applied to synthesis chiral heterocycles since 2019. It illustrates how much a diversity catalysts promote unprecedented domino reactions many types, allowing direct access wide variety complex and densely functionalized heterocyclic molecules.

Язык: Английский

Процитировано

2

Divergent Synthesis of Indolenine and Indoline Ring Systems by Palladium‐Catalyzed Asymmetric Dearomatization of Indoles** DOI
Dong Gao, Lei Jiao

Angewandte Chemie, Год журнала: 2022, Номер 134(13)

Опубликована: Янв. 26, 2022

Abstract Dearomatized indole derivatives bearing a C3‐ or C2‐stereocenter exist ubiquitously in natural products and biologically active molecules. Despite remarkable advances their synthesis, stereoselective regio‐divergent methods are still high demand. Herein, Pd‐catalyzed intermolecular asymmetric spiroannulation of 2,3‐disubstituted indoles with internal alkynes has been developed for the efficient construction indoline structures C2‐quaternary stereocenter. Stereospecific aza‐semipinacol rearrangement these under acidic conditions afforded indolenine C3‐quaternary stereocenter, where migrating group could be controlled by reaction sequence. The together subsequent enabled divergent access to dearomatized either

Язык: Английский

Процитировано

3

Palladium-Catalyzed Enantioselective Intramolecular Heck Dearomative Annulation of Indoles with N-Tosylhydrazones DOI Open Access
Yue Ma, Congcong Lu,

Sheng-Qi Xu

и другие.

Authorea (Authorea), Год журнала: 2024, Номер unknown

Опубликована: Янв. 30, 2024

An elegant Pd(dba)2-catalyzed enantioselective Heck dearomative annulation of indoles and N-tosylhydrazones for the straightforward assembly structurally diverse optically active indoline scaffolds containing quaternary carbon centers at C2-position has been developed. The tandem protocol, which utilized Pd(dba)2/BINOL-based phosphoramidite ligand as catalytic system, proceeded smoothly through successive oxidative addition, intramolecular palladation, migratory insertion, reductive elimination se-quences, leading to chiral derivatives in moderate excellent yields, with enantioselectivities diastereoselec-tivities. In synthetic practicability system was underlined by a scaled-up experiment late-stage derivatization products, thus highlighting potential applications chemistry, medicinal material science.

Язык: Английский

Процитировано

0