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

P-Stereogenic Phosphorus Ligands in Asymmetric Catalysis DOI
Tsuneo Imamoto

Chemical Reviews, Journal Year: 2024, Volume and Issue: 124(14), P. 8657 - 8739

Published: July 2, 2024

Chiral phosphorus ligands play a crucial role in asymmetric catalysis for the efficient synthesis of useful optically active compounds. They are largely categorized into two classes: backbone chirality and P-stereogenic ligands. Most reported belong to former class. Privileged ones such as BINAP DuPhos frequently employed wide range catalytic transformations. In contrast, latter class has remained small family many years mainly because their synthetic difficulty. The late 1990s saw emergence novel with superior enantioinduction ability Rh-catalyzed hydrogenation reactions. Since then, numerous have been synthesized used This Review summarizes thus far, including stereochemical electronic properties that afford high excellent enantioselectivities. Examples reactions use this described together applications construction key intermediates natural products therapeutic agents. literature covered dates back 1968 up until December 2023, centering on studies published later years.

Language: Английский

Citations

41
Recent advances in Pd-catalyzed asymmetric cyclization reactions DOI
Bing Xu,

Quanpu Wang,

Chao Fang

et al.

Chemical Society Reviews, Journal Year: 2023, Volume and Issue: 53(2), P. 883 - 971

Published: Dec. 18, 2023

This review aims to collect advancements in enantioselective palladium-catalyzed cyclization reactions over the past eleven years, and it is organized into thirteen sections depending on different types of transformations involved.

Language: Английский

Citations

41
Photoinduced Five‐Component Radical Relay Aminocarbonylation of Alkenes DOI
Bin Lu, Zhihan Zhang, Min Jiang

et al.

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(41)

Published: Aug. 24, 2023

Radical single carbonylation reactions with CO constitute a direct and robust strategy toward various carbonyl compounds from readily available chemicals, have been extensively studied over the past decades. However, realizing highly selective catalytic systems for controlled radical double has remained substantial challenge, particularly more advanced multicomponent variants, despite their great potential value. Herein, we report visible-light-driven relay five-component aminocarbonylation reaction of unactivated alkenes using under metal-free conditions. This protocol provides access to valuable γ-trifluoromethyl α-ketoamides good yields high chemoselectivity. Crucial was identification distinct dual roles amine coupling partners, sequentially acting as electron donors formation photoactive donor-acceptor (EDA) complexes precursors then acceptor via nitrogen cations form carbamoyl radicals. Cross-coupling radicals acyl that are formed in an alkene-based process affords products.

Language: Английский

Citations

25
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 International Edition, Journal Year: 2022, Volume and Issue: 61(17)

Published: Feb. 17, 2022

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

35
Recent Developments in Enantioselective Domino Reactions. Part A: Noble Metal Catalysts DOI

Hélène Pellissier

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(5), P. 620 - 681

Published: Jan. 17, 2023

Abstract This review updates the field of enantioselective domino reactions promoted by chiral catalysts derived from noble metals, including palladium, silver, rhodium, ruthenium, iridium and gold, published since beginning 2019. It illustrates how much a diversity these allow unprecedented asymmetric many types to be achieved with excellent enantioselectivity, giving direct access wide variety complex molecules. magnified image

Language: Английский

Citations

22
Catalysis and Synthesis Enabled by P-Chiral Dihydrobenzooxaphosphole Ligands DOI
Zhen Cao, Dongyang He, Wenjun Tang

et al.

Organic Process Research & Development, Journal Year: 2024, Volume and Issue: 28(4), P. 949 - 977

Published: April 8, 2024

P-Chiral phosphorus ligands received little attention in organic chemistry until Knowles made his landmark contribution asymmetric hydrogenation by developing the P-chiral CAMP and DIPAMP. The development of accelerated end last century with advent some highly efficient renowned for hydrogenation, including BisP*, TangPhos, QuinoxP*, DuanPhos, et al. However, most reported were air-sensitive, difficult to make, or lacked structural modularity, hampering their availability applicability. sterically electronically tunable is particularly desirable. Over past decade, a family hindered, electron-rich, structurally tunable, air-stable dihydrobenzooxaphosphole emerged that proved be versatile various transformations. 5 years witnessed an increasing number studies related these discovery unprecedented catalytic properties This review highlights unique catalysis applications synthesis natural products therapeutic agents.

Language: Английский

Citations

5
Regioselective C–H Active Carbonylation via 1,4-Palladium Migration DOI
Ming Li,

Shun‐Xi Li,

Dong‐Ping Chen

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(16), P. 2761 - 2766

Published: April 13, 2023

We report a highly regioselective three-component coupling reaction of styrene, CO gas, and an amine compound to synthesize multisubstituted α,β-unsaturated amides, which involves palladium-catalyzed sequential 1,4-palladium migration, C(sp2)-H activation, carbonylation, amination. Salient features this strategy include the use 1 atm CO, excellent stereochemistry, good functional group tolerance. Further, series control experiments density theory calculations were performed afford some insights for transfer mechanism.

Language: Английский

Citations

11
Synthesis of 7-Arylthiomethyl Dibenzo[b,d]azepines through Imidoylative Heck Cyclization and CPA-Catalyzed Thio-Michael Addition/Enantioselective Protonation DOI
Weiming Hu, Xilong Wang, Yan Peng

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(20), P. 3642 - 3646

Published: May 13, 2022

A chiral phosphoric acid-catalyzed thio-Michael addition/enantioselective protonation has been developed for the first time. The reaction applies 7-methylene-6-aryl-7H-dibenzo[b,d]azepines, products of Pd-catalyzed imidoylative Heck cyclization, as Michael acceptors in reactions with a wide range aryl thiols. Diversified 7-[(arylthio)methyl]-7H-dibenzo[b,d]azepines bearing benzylic stereocenter and thermodynamically regulated biaryl axis were produced good to excellent enantioselectivity 14–25:1 diastereoisomeric ratios.

Language: Английский

Citations

17
Enantioselective Palladium-Catalyzed Domino Carbonylative Heck Esterification of o-Iodoalkenylbenzenes with Arylboronic Acids DOI

Yaodu Zhang,

Ming Chen, Yang Li

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(45), P. 8110 - 8115

Published: Nov. 3, 2023

The current investigation presents an innovative palladium-catalyzed asymmetric carbonylative Heck esterification method. This approach facilitates the efficient synthesis of various chiral γ-ketoacid esters by utilizing o-alkenyliodobenzenes and arylboronic acids as primary substrates. reaction achieves creation three carbon–carbon bonds, two carbon–oxygen establishment a quaternary carbon center within single step. α-chiral were obtained in yields ranging from good to high yields, displaying enantiomeric excesses (ee's) levels up 92% under mild conditions.

Language: Английский

Citations

10
Recent Advances in the Catalytic Synthesis of α‐Ketoamides DOI

Mathew B. Aaron,

P. Devi, Gopinathan Anilkumar

et al.

The Chemical Record, Journal Year: 2025, Volume and Issue: unknown

Published: April 21, 2025

Abstract α ‐Ketoamides are privileged chemical entities featuring a carbonyl group bonded to an amide. Bearing two pronucleophilic and proelectrophilic sites, this structural scaffold exhibits distinct properties unparalleled biological activity. Owing its wide application in medicinal, agricultural, synthetic chemistry, methods for assembling moiety ever‐growing demand. With the increasing focus on green synthesis, traditional routes ‐ketoamides have faded recent years giving rise development of photocatalytic, electrosynthetic, microwave‐assisted catalytic protocols. We hereby provide comprehensive critical summary all advancements witnessed field from 2016 present.

Language: Английский

Citations

0