Pd-Catalyzed Sequential Intramolecular Annulation/ Intermolecular [3+2] Cycloaddition of 5-Allenyloxazolidine-2,4-diones with Dipoles: Synthesis of Spiroheterocycles DOI
Yujie Dong, Jun Liu,

Rongjin Ning

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(76), P. 10516 - 10519

Published: Jan. 1, 2024

Pd-catalyzed sequential intramolecular annulation/intermolecular [3+2] cycloaddition of 5-allenyloxazolidine-2,4-diones with dipoles was achieved. Under palladium catalysis, various reacted 1,3-dipoles such as nitrile

Language: Английский

Palladium(0) π-Lewis Base Catalysis: Concept and Development DOI
Zhichao Chen, Qin Ouyang, Wei Du

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(10), P. 6422 - 6437

Published: March 1, 2024

The development of a new catalytic strategy plays vital role in modern organic chemistry since it permits bond formation an unprecedented and more efficient manner. Although the application preformed metal complexes as π-base-activated reagents have enabled diverse transformations elegantly, concept by directly utilizing transition metals π-Lewis base catalysts remain underdeveloped, especially field asymmetric catalysis. Here, we outline our perspective on discovery palladium(0) catalyst, which is capable increasing highest occupied molecular orbital (HOMO) energy both electron-neutral electron-deficient 1,3-dienes 1,3-enynes upon flexible η2-complexes formed situ resultant π-backdonation. Thus, fruitful carbon–carbon-forming reactions with electrophiles can be achieved enantioselectively vinylogous addition pattern, conceptually different from classical oxidative cyclization mechanism. Emphasis will given to mechanism elucidation, features, reaction design together further this emerging field.

Language: Английский

Citations

14
Base‐Mediated Four‐Component Intramolecular Cyclization reaction: One‐pot Access to Imidazole‐4‐(2H)‐ones DOI Open Access

Ganesh P. Pawar,

Indrajeet J. Barve, Li‐Ching Shen

et al.

Advanced Synthesis & Catalysis, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 22, 2025

Abstract A base‐mediated one‐pot, two‐step, four‐component reaction has been developed to synthesize imidazole‐4(2 H )‐ones, utilizing commercially available amino acid esters, aldehydes, alkynes, and alcohols. Control experiments isolation of the intermediate revealed mechanistic details. This proceeds via imine formation, followed by nucleophilic addition alkyne form a propargylamine precursor. Subsequently, precursor under undergoes conversion into 1‐azadiene, in situ ketene formation generate (allylideneamino)prop‐1‐en‐1‐one. The alcohol subsequent intramolecular cyclization provides imidazole‐4 (2 )‐ones exclusively.

Language: Английский

Citations

1
4-Vinylbenzodioxinones as a new type of precursor for palladium-catalyzed (4+3) cycloaddition of azomethine imines DOI
Yi Tang,

Rulei Zhang,

Yujie Dong

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(11), P. 1436 - 1439

Published: Jan. 1, 2024

Benzo-fused cyclic carbonates were designed and synthesized as a novel type of precursor π-allylpalladium zwitterionic intermediates.

Language: Английский

Citations

8
Pd-catalyzed exclusively regioselective [5 + 4] cycloaddition for the construction of 1,5-di/ox-azonanes DOI
Wenqi Liu,

Meng Zang,

Jian Zhang

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(7), P. 1680 - 1685

Published: Jan. 1, 2023

An efficient approach for the exclusively regioselective construction of 1,5-di/ox-azonanes via Pd-catalyzed [5 + 4] cycloaddition has been developed.

Language: Английский

Citations

13
Facile Synthesis of Quinoline-Substituted 3-Hydroxy-2-oxindoles and 3-Amino-2-oxindoles via a Palladium-Catalyzed Cascade Intramolecular Cyclization/Intermolecular Nucleophilic Addition Reaction DOI

Huawei Lin,

Xinyan Hu, Bing Han

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(5), P. 3413 - 3418

Published: Feb. 20, 2024

An efficient cascade intramolecular cyclization/intermolecular nucleophilic addition reaction of allenyl benzoxazinone with isatin or isatin-derived ketimine has been established by using Pd0-π-Lewis base catalysis. A series 3-hydroxy-2-oxindoles and 3-amino-2-oxindoles quaternary carbon atoms at the C3 position were synthesized in good yields under mild conditions through this protocol.

Language: Английский

Citations

4
Palladium-catalyzed asymmetric [4 + 3] cycloaddition of methylene-trimethylenemethane: access to seven-membered exocyclic axially chiral allenes DOI Creative Commons
Yafei Wu, Zhuo Wang,

Yuqian Shan

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: 15(25), P. 9703 - 9708

Published: Jan. 1, 2024

A palladium-catalyzed asymmetric [4 + 3] cycloaddition of the methylene-trimethylenemethane donor with an azadiene has been developed, affording benzofuro[3,2- b ]azepine-derived exocyclic chiral allene control axial and point chirality.

Language: Английский

Citations

4
Cu-Catalyzed Divergent Transformations of Allenylethylene Carbonates with Diboron Reagents DOI

Si-Jie Chen,

Xiaojie Su, Yujie Dong

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(4), P. 960 - 965

Published: Jan. 19, 2024

Divergent transformations of allenylethylene carbonates with diboron reagents catalyzed by copper are disclosed. By using CuCl/IPr·HCl as the catalyst, react B2hex2 to afford 2,4-dien-1-ols product in presence Cs2CO3 base, iPrOH additive, and 1,4-dioxane solvent. And they B2pin2 form boronic half acids NaOtBu water THF The reactions corresponding products good stereoselectivities yields, further derivatizations study mechanism also demonstrated.

Language: Английский

Citations

3
Palladium-catalyzed [6 + 4] cycloaddition with π-allyl all-carbon 1,6-dipole for the synthesis of ten-membered heterocycles DOI
Juntao Chen, Na Lin, Linli Xu

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 11(5), P. 1299 - 1304

Published: Dec. 25, 2023

This work introduces a novel α,α-diester-δ-vinylvalerolactone as dipolar precursor in palladium-catalyzed [6 + 4] cycloaddition reaction with azadienes, resulting the production of ten-membered heterocycles.

Language: Английский

Citations

8
Advancements in Asymmetric Catalytic Approaches Involving Benzoxazinone Derivatives DOI Open Access
Ruilin Zhang,

Kaixiong Qiu,

Hongfei Gao

et al.

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(17), P. 2767 - 2788

Published: July 10, 2023

Abstract Chiral aza ‐heterocycles, as a sort of key frameworks natural products et al , are deeply concerned by synthetic chemists. In recent years, catalytic asymmetric reactions several types zwitterionic intermediates, originating form benzoxazinone derivatives, have become popular and efficient approach to obtain chiral ‐heterocycles. Given that, this review attempts summarize development in the field derivatives powerful dipole precursors for construction past various their been developed. Herein, is organized display important potentials values.

Language: Английский

Citations

7
Palladium-catalyzed [4+4] cycloaddition of 2-pyrones with 2-alkylidenetrimethylene carbonates: access to bridged eight-membered oxygen heterocycles DOI

Huawei Lin,

Biming Mao, Bing Han

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(10), P. 2864 - 2869

Published: Jan. 1, 2024

A novel palladium-catalyzed [4 + 4] cycloaddition of 2-pyrones with 2-alkylidenetrimethylene carbonates has been developed for the synthesis bridged eight-membered oxygen heterocycles in good yields and excellent stereoselectivities.

Language: Английский

Citations

2