Palladium‐Catalyzed Oxidative Carbonylation of Diarylamines for the Synthesis of Acridone Derivatives DOI
Wenting Guo, Wenting Wu,

Jiali Huang

et al.

Asian Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 13(4)

Published: Dec. 15, 2023

Abstract A Pd‐catalyzed oxidative dual C−H carbonylation has been developed starting from commercially available diarylamines, in which the Cr(CO) 6 served as a safe carbonyl source. This method provides facile and atom‐economic approach toward diversified acridone derivatives moderate to good yields, features with functional group compatibility, operational safety easy scale‐up.

Language: Английский

Switching from gem-difluorovinylation to carboxylation: ligand-enabled palladium-catalyzed Heck annulation of alkene-tethered aryl halides with sodium difluorochloroacetate DOI
Yu Xia, Wenqi Li,

Minzhu Wei

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(12), P. 3491 - 3496

Published: Jan. 1, 2024

The use of a ligand to tune palladium-catalyzed intramolecular Heck gem -difluorovinylation and carboxylation is reported. Sodium difluorochloroacetate (ClCF 2 COONa) acts as both difluorocarbene (:CF ) carboxyl source.

Language: Английский

Citations

2

Construction of Benzofuran‐3(2H)‐one Scaffolds bearing a C2 Quaternary Center via Palladium‐Catalyzed Carbonylative Heck Reaction using Mo(CO)6 as Carbonyl Source DOI
Wenting Guo,

Houhong Gong,

Xiaojing Jiao

et al.

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

Published: July 2, 2024

Abstract A Pd‐catalyzed carbonylative Heck reaction of 2‐iodophenyl alkenyl ether using Mo(CO) 6 as a safe CO source has been developed. This research provides an atom‐economic and straightforward route for the efficient construction benzofuran‐3(2 H )‐one scaffolds with C2 quaternary center in moderate to good yields, which features operational safety, functional group compatibility easy scale‐up.

Language: Английский

Citations

2

De Novo Synthesis of α‐Ketoamides via Pd/TBD Synergistic Catalysis DOI Creative Commons
Jiahe Chen,

Li‐Ren Zhang,

Zhang‐Yang Wang

et al.

Advanced Science, Journal Year: 2024, Volume and Issue: unknown

Published: July 10, 2024

Precisely controlling the product selectivity of a reaction is an important objective in organic synthesis. α-Ketoamides are vital intermediates chemical transformations and privileged motifs numerous drugs, natural products, biologically active molecules. The selective synthesis α-ketoamides from feedstock chemicals safe operationally simple manner under mild conditions long-standing catalysis challenge. Herein, unprecedented TBD-switched Pd-catalyzed double isocyanide insertion for assembling ketoamides aqueous DMSO (hetero)aryl halides pseudohalides reported. effectiveness utility this protocol demonstrated by its diverse substrate scope (93 examples), ability to late-stage modify pharmaceuticals, scalability large-scale synthesis, pharmaceutically Mechanistic studies indicate that TBD key ligand modulates process, thereby selectively providing desired unique manner. In addition, imidoylpalladium(II) complex α-ketoimine amide successfully isolated determined X-ray analysis, confirming they probable catalytic pathway.

Language: Английский

Citations

2

Recent Advances in the Synthesis of Five‐membered Nitrogen Heterocycles Induced by Palladium Ions and Complexes DOI
Árpàd Molnár

ChemistrySelect, Journal Year: 2023, Volume and Issue: 8(6)

Published: Feb. 8, 2023

Abstract This review aims to collect and analyze recent results with respect the use of varied palladium preparations in synthesis five‐membered nitrogen heterocycles including condensed derivatives. Results have been selected focus on studies last three years. Furthermore, a common feature all methods treated here is that nitrogen‐containing ring formed via closing appropriate starting materials. Selected examples discussed will reveal plethora products from small monocycles multi‐ring systems can be successfully accessed. Major features are wide product ranges, high yields stereoselectivities often achieved under mild reaction conditions.

Language: Английский

Citations

6

Palladium-Catalyzed Carbonylative Dearomatization of Indoles to Achieve Carbonyl-Containing Spirocyclic Indolenines Bearing an All-Carbon Quaternary Center DOI
Weiming Hu,

Jiali Huang,

Jingyu Yao

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(32), P. 5951 - 5956

Published: Aug. 3, 2023

A Pd-catalyzed carbonylative dearomatization via an acyl Pd complex has been developed. Diversified carbonyl-containing spirocyclic indolenines with all-carbon quaternary center were constructed in efficient and straightforward way good to excellent yields. The protocol features a simple catalytic system, operational simplicity, broad substrate scope, easy scale-up, versatile transformations. In addition, the asymmetric reaction was initially explored moderate enantioselectivity.

Language: Английский

Citations

6

Copper‐Catalyzed Substrate‐Controlled Carbonylative Synthesis of α‐Keto Amides and Amides from Alkyl Halides DOI
Fengqian Zhao, Han‐Jun Ai, Xiao‐Feng Wu

et al.

Angewandte Chemie, Journal Year: 2022, Volume and Issue: 134(17)

Published: Feb. 17, 2022

Abstract Controllable production of α‐keto amides and from the same substrates is an attractive goal in field transition‐metal‐catalyzed (double‐)carbonylation. Herein, a novel copper‐catalyzed highly selective double carbonylation alkyl bromides has been developed. Moderate to good yields were obtained as only products. In case iodides, double‐ mono‐carbonylation can be achieved controllably under different conditions.

Language: Английский

Citations

9

Radical Cascade Annulation of Biphenyl Acrylamides to Dibenzoazepinones: Experimental and DFT Studies DOI

Raju Dupud,

Ramakrishnan Thushara,

Karthik Kumar Merugu

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(31)

Published: June 6, 2024

Abstract An efficient method for the conversion of biphenyl acrylamides to dibenzoazepinones with −SCF 3 incorporation is described. This operationally simple radical cascade reaction employs CAN as an oxidant and exhibits good functional group tolerance. Substrates featuring −OCH , −CH −Br or −Cl at para ‐position aromatic ring a preference ipso ‐cyclization due intervention DMSO in reaction. Density theory (DFT) calculations provide valuable insights into reaction's energetics product selectivity.

Language: Английский

Citations

1

Application of Carbonylation in the Synthesis of Bulk and Fine Chemicals DOI

Huibing Shi,

Yaowei Wang, Peng Wang

et al.

Chinese Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 44(6), P. 1811 - 1811

Published: Jan. 1, 2024

Language: Английский

Citations

1

Synthesis of N‐Aryl α‐Ketoamides, α‐Ketoesters, α‐Ketothioesters and Their Applications in Quinoxalinone Preparation DOI
Shweta Singh, Popuri Sureshbabu, Shahulhameed Sabiah

et al.

Asian Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 11(5)

Published: April 4, 2022

Abstract Synthesis of N‐ aryl α ‐ketoamides, ‐ketoesters and ‐ketothioesters were demonstrated from Ts Boc ‐ketoamides via transamidation transesterification reactions. The reactions proceeded at room temperature in the presence DBU provided desired products good to excellent yields a short time. A regioselective synthesis biologically relevant quinoxalinones was achieved nitration followed by reduction

Language: Английский

Citations

6

Palladium-Catalyzed Carbonylative Hiyama–Denmark Reaction toward the Synthesis of Aryl Carbonyl-Containing Oxindoles DOI

Xiong Li,

Xuemei Zhang, Baojian Xiong

et al.

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 88(8), P. 5226 - 5230

Published: Dec. 29, 2022

A palladium-catalyzed domino Heck cyclization/carbonylative Hiyama-Denmark cross-coupling reaction between alkene-tethered aryl iodides and silylcarboxylic acids is presented. This proceeds well without toxic carbon monoxide (CO) gas has good functional group tolerance, providing an alternative access to carbonyl-containing oxindoles. In this transformation, play a dual role as CO source nucleophile.

Language: Английский

Citations

5