Acid-Regulated Selective Synthesis of Benzofuran Derivatives via Single-Component BDA Retro-Aldol/Michael Addition Cascade and [4 + 2] Cycloaddition Reactions DOI
Shuhong Wang,

X. Y. Niu,

Hongbin Zhou

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: May 20, 2025

The acid-controlled single-component retro-aldol/Michael addition cascade reaction and [4 + 2] cycloaddition of benzofuran-derived azadienes (BDAs) are reported for the first time. Under conditions trifluoromethanesulfonic acid as catalyst with water, BDAs initiate retro-aldol reaction, followed by a 1,4-Michael addition, yielding (arylmethylene)bis(dibenzofuran) products excellent yields broad substrate applicability. This represents application in reaction. In contrast, absence water boron trifluoride etherate catalyst, undergo constructing spiro[benzofuran-2,3'-benzofuro[3,2-b]pyridine] framework high diastereoselectivity. method features mild atom economy, provides new approach benzofuran scaffold derivatives.

Language: Английский

High-order dipolar annulations with metal-containing reactive dipoles DOI
Mao‐Mao Zhang,

Bao‐Le Qu,

Bin Shi

et al.

Chemical Society Reviews, Journal Year: 2022, Volume and Issue: 51(10), P. 4146 - 4174

Published: Jan. 1, 2022

The advances on metal-catalysed high-order dipolar annulations were comprehensively summarized in this review. To further exploit the potential of unique annulation strategy, a research outlook was also proposed.

Language: Английский

Citations

88

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

42

Recent advances of Pd-π-allyl zwitterions in cycloaddition reactions DOI
Juan Du, Yunfan Li, Chang‐Hua Ding

et al.

Chinese Chemical Letters, Journal Year: 2023, Volume and Issue: 34(11), P. 108401 - 108401

Published: March 30, 2023

Language: Английский

Citations

25

Enantio‐, Diastereo‐ and Regioselective Synthesis of Chiral Cyclic and Acyclic gem‐Difluoromethylenes by Palladium‐Catalyzed [4+2] Cycloaddition DOI

Hiroto Uno,

Koki Kawai,

Taichi Araki

et al.

Angewandte Chemie International Edition, Journal Year: 2022, Volume and Issue: 61(24)

Published: March 28, 2022

gem-Difluoromethylene moieties are attractive in medicinal chemistry due to their ability mimic other more ubiquitous functional groups. Thus, effective asymmetric methods for construction highly desirable, especially the industrial production of chiral drugs. Using a Pd-catalyzed [4+2] cycloaddition between substituted-2-alkylidenetrimethylene carbonates and gem-difluoroalkyl ketones, we were able easily access 1,3-dioxanes that contain tetrasubstituted difluoroalkyl stereogenic center cyclic acyclic skeletons. A novel phosphoramidite ligand, which contains bulky 1,1-dinaphthylmethanamino moiety, was developed provide products high yield with excellent enantio-, diastereo-, regioselectivity. Strikingly, gem-difluoro substitution pattern promotes reaction, pentafluoroethylketone, an α,α-difluorinated β-ketoester, β-ketosulfone suitable substrates this method.

Language: Английский

Citations

32

Recent advances in ligand-enabled palladium-catalyzed divergent synthesis DOI
Yue Wang,

Jinzan Feng,

Er‐Qing Li

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 22(1), P. 37 - 54

Published: Nov. 27, 2023

Developing efficient and straightforward strategies to rapidly construct structurally distinct diverse organic molecules is one of the most fundamental tasks in synthesis, drug discovery materials science. In recent years, divergent synthesis functional from same starting has attracted significant attention been recognized as an powerful strategy. To achieve this objective, proper adjustment reaction conditions, such catalysts, solvents, ligands, etc., required. review, we summarized efforts chemo-, regio- stereodivergent reactions involving acyclic cyclic systems catalyzed by palladium complexes. Meanwhile, types, including carbonylative reactions, coupling cycloaddition well probable mechanism have also highlighted detail.

Language: Английский

Citations

14

Enantioselective Construction of Eight‐Membered N‐Heterocycles from Simple 1,3‐Dienes via Pd(0) Lewis Base Catalysis DOI

Jiaoting Pan,

Takumi Ogawa Ho,

Ying‐Chun Chen

et al.

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 63(6)

Published: Dec. 15, 2023

Abstract We report herein an unprecedented enantioselective (4+4) cycloaddition of simple 1,3‐dienes with azadienes for the construction fused eight‐membered N ‐heterocycles. In this transformation, π‐Lewis basic Pd(0) catalyst achieves activation to induce nucleophilic addition followed by ring cyclization via a selective terminal allylic substitution. Furthermore, highly efficient and diastereoselective derivatizations rings provide facile access diverse enantiopure tetra‐ hexacyclic compounds potential application in medicinal chemistry.

Language: Английский

Citations

14

Transition Metal-Catalyzed Asymmetric Cyclizations Involving Allyl or Propargyl Heteroatom-Dipole Precursors DOI Open Access
Jian Zhang, Ying Chen, Quannan Wang

et al.

Chinese Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 42(10), P. 3051 - 3051

Published: Jan. 1, 2022

Chiral heterocyclic compounds are an important class of chiral substances, which widespread in many drugs, pesticides and catalysts.Therefore, the efficient asymmetric synthesis these becomes a research hotspot organic synthesis.Transition metal-catalyzed cyclization with heteroatom-dipole precursors is method to construct frameworks.Among them, designed based on transition allyl or propargyl substitutions have been extensively studied past two decades occupied role this field.The cyclizations introduced detail.The advantages existing problems current methods analyzed, would provide useful reference for researchers related fields.

Language: Английский

Citations

22

Palladium‐Catalyzed [4+2] Cycloaddition of Hydroxy‐Tethered Allylic Carbonates with Alkenes: Synthesis of Functionalized Tetrahydropyrans DOI Open Access

Jiaqing Xu,

Wangyu Shi,

Min Liu

et al.

Advanced Synthesis & Catalysis, Journal Year: 2022, Volume and Issue: 364(12), P. 2060 - 2066

Published: May 5, 2022

Abstract A palladium‐catalyzed [4+2] cycloaddition of hydroxy‐tethered allyl carbonates with five types electron‐deficient alkenes has been achieved, in which a type new acted as valuable precursors for the formation 1,4‐C,O‐dipole allylpalladium intermediates. The reaction proceeded efficiently under mild conditions to provide corresponding tetrahydropyran derivatives moderate high yields excellent diastereoselectivities. magnified image

Language: Английский

Citations

21

Rigid P-Chiral Phosphorus Ligands for Highly Selective Palladium-Catalyzed (4+2) and (4+4) Annulations DOI

Yinggao Meng,

Qian Wang, Xinyu Yao

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(50), P. 9205 - 9209

Published: Dec. 12, 2022

We developed novel shackled P-chiral ligands based on 1-phosphanorbornenes and oxazolines. They were subsequently evaluated in palladium-catalyzed (4+2) annulations, producing enantioenriched tetrahydropyran scaffolds good yields with high site selectivity enantioselectivity. Moreover, chemoselective (4+4) products also achieved by using acyclic imines. In addition, density functional theory calculations performed to afford the energy profile of Michael addition step ring formation step. This demonstrated that enantioselective annulations reaction between mostly under thermodynamic control.

Language: Английский

Citations

20

Palladium‐Catalyzed [4 + 4] Cycloaddition of Homo‐TMM All‐Carbon 1,4‐Dipole Precursors for Construction of Benzofuro[3,2‐b]azocines and Furo[3,2‐b]azocines DOI
Ying Chen,

Meng Zang,

Weijie Wang

et al.

Chinese Journal of Chemistry, Journal Year: 2023, Volume and Issue: 41(21), P. 2825 - 2831

Published: June 25, 2023

Comprehensive Summary We developed a novel Pd‐catalyzed [4 + 4] cycloaddition of (benzo)furan‐derived azadienes with homo‐TMM all‐carbon 1,4‐dipoles in situ generated from α ‐allyl malonate derivatives, affording an array benzofuro[3,2‐ b ]azocines and furo[3,2‐ good to excellent yields (up 96%) exclusive regioselectivities. This methodology featured mild reaction conditions functional group tolerance. The synthetic utility was demonstrated by gram‐scale reaction. Furthermore, the catalytic asymmetric version has also been explored.

Language: Английский

Citations

13