A Cascade C(sp3)−H Annulation Involving C(alkyl),C(alkyl)‐Palladacycle Intermediates DOI
Liwei Zhou,

Xiahong Chen,

Qiong Peng

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: 136(45)

Published: July 25, 2024

Abstract C−H bond functionalization involving C , ‐palladacycle intermediates provides a unique platform for developing novel reactions. However, the vast majority of studies have been limited to transformations (aryl), ‐palladacycles. In sharp contrast, catalytic reactions (alkyl), (alkyl)‐palladacycles rarely reported. Herein, we disclose an unprecedented cascade C(sp 3 )−H annulation (alkyl)‐palladacycles. this protocol, alkene‐tethered cycloalkenyl bromides undergo intramolecular Heck/C(sp activation generate (alkyl)‐palladacycles, which can be captured by α ‐bromoacrylic acids afford tricyclic fused pyridinediones. addition, strategy also applied indole‐tethered construct pentacyclic pyridinediones via suquential Heck dearomatization/C(sp activation/decarboxylative cyclization. Notably, removal in reaction build interesting skeleton containing four‐membered ring. Preliminary mechanistic experiments indicate that five‐membered serve as key intermediates. Meanwhile, density functional theory (DFT) calculations provided insights into pathway.

Language: Английский

A palladium-catalyzed cross-electrophile coupling reaction involving sulfur dioxide for the direct synthesis of diversely functionalized sulfones DOI
Baojian Xiong, Jinyu Zhang, Ting Wang

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(14), P. 3567 - 3576

Published: Jan. 1, 2023

A palladium catalyzed multi-component cross-electrophile coupling involving sulfur dioxide is presented here. This protocol features mild reaction conditions, wide substrate scope, good functional group tolerance and excellent regioselectivity.

Language: Английский

Citations

12

A Cascade C(sp3)−H Annulation Involving C(alkyl),C(alkyl)‐Palladacycle Intermediates DOI Open Access
Liwei Zhou,

Xiahong Chen,

Qiong Peng

et al.

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

Published: July 25, 2024

Abstract C−H bond functionalization involving C , ‐palladacycle intermediates provides a unique platform for developing novel reactions. However, the vast majority of studies have been limited to transformations (aryl), ‐palladacycles. In sharp contrast, catalytic reactions (alkyl), (alkyl)‐palladacycles rarely reported. Herein, we disclose an unprecedented cascade C(sp 3 )−H annulation (alkyl)‐palladacycles. this protocol, alkene‐tethered cycloalkenyl bromides undergo intramolecular Heck/C(sp activation generate (alkyl)‐palladacycles, which can be captured by α ‐bromoacrylic acids afford tricyclic fused pyridinediones. addition, strategy also applied indole‐tethered construct pentacyclic pyridinediones via suquential Heck dearomatization/C(sp activation/decarboxylative cyclization. Notably, removal in reaction build interesting skeleton containing four‐membered ring. Preliminary mechanistic experiments indicate that five‐membered serve as key intermediates. Meanwhile, density functional theory (DFT) calculations provided insights into pathway.

Language: Английский

Citations

5

Recent advances in the palladium-catalyzed sulfonylation via SO2 insertion DOI
Yujiao Zhang,

Meng-Ling Li,

Haixia Hu

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(29), P. 5868 - 5885

Published: Jan. 1, 2024

The importance of sulfonyl-group-containing compounds, such as sulfonamides, sulfones, sulfinate esters, and sulfonyl fluorides, in pharmaceuticals, bioactive molecules, natural products cannot be overstated. new development palladium-catalyzed sulfonylation

Language: Английский

Citations

4

Palladium-Catalyzed Dearomative Heck/C(sp2)–H Activation/Decarboxylative Cyclization of C2-Tethered Indoles DOI
Shuyi Guo,

Wenbo Deng,

Xiaochang Xiao

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(43), P. 9389 - 9394

Published: Oct. 21, 2024

Until now, palladium-catalyzed dearomative Heck reactions of indoles were largely limited to β-H elimination and nucleophilic capture the transient alkyl-Pd(II) species. Herein, we disclose a novel Heck/C(sp

Language: Английский

Citations

3

Palladium-Catalyzed Domino Heck/Decarboxylative Cyanomethylation of Indoles and Alkenes with Cyanoacetate Salts DOI

Ping‐Xin Zhou,

Yang Liu, Mengjuan Li

et al.

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

Published: April 10, 2025

A palladium-catalyzed reaction of indoles with cyanoacetate salts enables the synthesis 2,6-disubstituted indolines via tandem dearomatization/decarboxylative cyanomethylation. Remarkably, this is first example indole difunctionalization at C2 and C6 positions. Moreover, methodology extends to cyclization/decarboxylative cyanomethylation aryl halide-tethered alkenes.

Language: Английский

Citations

0

Palladium-catalyzed domino cyclization/direct functionalization involving the insertion of SO2 DOI
Xinwei Zhang,

Yaoyao Lu,

Shuoshuo Zhang

et al.

New Journal of Chemistry, Journal Year: 2024, Volume and Issue: 48(12), P. 5101 - 5106

Published: Jan. 1, 2024

A reductive cross-coupling strategy for the synthesis of sulfone-containing oxindoles was presented. Moreover, using amines instead alkyl bromides, a palladium-catalyzed domino cyclization/aminosulfonylation also established.

Language: Английский

Citations

3

Synthesis of condensed tetra- and polycyclic nitrogen heterocycles with a five-membered azacyclic core induced by ionic palladium catalysts DOI
Árpàd Molnár

Coordination Chemistry Reviews, Journal Year: 2024, Volume and Issue: 504, P. 215668 - 215668

Published: Jan. 19, 2024

Language: Английский

Citations

2

Palladium-Catalyzed Reductive Cross-Coupling of Propargyl Acetates with Aryl Iodides Involving the Insertion of SO2 DOI
Qian Zhang,

Yaolu Ying,

Hongyin Zhang

et al.

Chinese Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 44(6), P. 2033 - 2033

Published: Jan. 1, 2024

Language: Английский

Citations

2

Palladium-catalyzed three-component Heck/sulfonation/amination leading to quaternary 3,4-dihydroisoquinolinones DOI
Yujiao Zhang,

Liang-Yuan Pu,

Yimiao He

et al.

Tetrahedron Letters, Journal Year: 2022, Volume and Issue: 112, P. 154240 - 154240

Published: Nov. 8, 2022

Language: Английский

Citations

3

Dearomatization of indoles via palladium-catalyzed carbonylation using Co2(CO)8 as the carbonyl source leading to carbonyl-containing spiroindolenines DOI
Weiming Hu,

Jiali Huang,

Wenting Wu

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(20), P. 5242 - 5247

Published: Jan. 1, 2023

A Pd-catalyzed carbonylative dearomatization of indoles using Co 2 (CO) 8 as a safe CO source has been reported.

Language: Английский

Citations

1