Aryl‐to‐Vinyl 1,4‐Nickel Migration/Reductive Cross‐Coupling Reaction for the Stereoselective Synthesis of Multisubstituted Olefins DOI Open Access

Cui‐Tian Wang,

Peng‐Yu Liang,

Ming Li

и другие.

Angewandte Chemie, Год журнала: 2023, Номер 135(28)

Опубликована: Май 5, 2023

Abstract The aryl‐to‐vinyl nickel 1,4‐migration (1,4‐Ni migration) reaction has been reported for the first time. generated alkenyl Ni species undergo a reductive coupling with unactivated brominated alkanes affording series of trisubstituted olefins. This tandem exhibits mild conditions, broad substrate scope, high regioselectivity, and excellent Z / E stereoselectivity. A controlled experiments have shown that critical 1,4‐Ni migration process is reversible. In addition, intermediates obtained after are highly stereoselective do not isomerization. trace isomerization products caused by instability product.

Язык: Английский

Metal‐Catalyzed Coupling of N‐Tosylhydrazones with Compounds Containing C‐H/Heteroatom‐H Bonds DOI

Akanksha Akanksha,

Ajaya Kumar Singh,

Anupama Asthana

и другие.

Asian Journal of Organic Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Авг. 16, 2024

Abstract The present review covers various advances in the field of metal‐catalyzed coupling N ‐tosylhydrazones with compounds containing C−H/heteroatom‐H bonds, including transition metal catalysts i. e., Pd, Rh, Cu, Ag, Ni and Co resulting alkylated, alkenylated, alkynylated, allenylated, annulated many other products. A carbene migratory insertion process play a key role carbon‐carbon single bond (C−C) double (C=C) formation undergoes variety cascade reactions to synthesize wide scope pharmaceutically medicinally valuable scaffoldings.

Язык: Английский

Процитировано

2

Stereoselective Construction of Trisubstituted 1,3‐Enynes <i>via</i> Aryl to Vinyl 1,4‐Palladium Migration DOI Open Access
Jie Lin, Juan Ma, Liandi Wang

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(21), С. 4509 - 4514

Опубликована: Авг. 2, 2024

Abstract Palladium‐catalyzed stereoselective olefinic C−H alkynylation of gem ‐diarylsubstituted ethylenes with propargylic alcohols was achieved to access diverse unsymmetrical 1,3‐enynes. The regio‐ and stereoselectivities were established through a 1,4‐palladium migration from aryl vinyl in the presence 2‐FC 6 H 4 OH as additive. Mechanistic investigations suggest that cleavage bond might not be involved rate‐determining step catalytic process.

Язык: Английский

Процитировано

2

Regioselective polyfluoroarylation of alkenyl C–H bonds via aryl to vinyl 1,4-palladium migration DOI
Jie Lin, Juan Ma, Liandi Wang

и другие.

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(20), С. 5144 - 5150

Опубликована: Янв. 1, 2023

Efficient palladium-catalyzed regioselective vinylic C–H polyfluoroarylation of gem -disubstituted ethylenes with polyfluoroarenes was realized via an aryl to vinyl 1,4-palladium migration process access various polyfluorinated triarylethenes.

Язык: Английский

Процитировано

5

Research Progress of Transition Metal Catalyzed Synthesis of 1,3- Conjugated Diene Compounds from Alkenes and Alkynes DOI Open Access

Guangli Xu,

Jing Xu,

Haidong Xu

и другие.

Chinese Journal of Organic Chemistry, Год журнала: 2023, Номер 43(6), С. 1899 - 1899

Опубликована: Янв. 1, 2023

1,3-Conjugated dienes are key structural units of many natural products and drugs.Conjugated alkenes also play a central role in organic synthesis materials science due to their special chemical properties.At present, the 1,3-conjugated diene is mainly achieved by transition metal catalysis, researchers have constructed series 1,3-diene skeletons through this method, which enriches diversity conjugated compounds extends application range compounds.The reviewed classification based on different types catalysts, its development prospects prospected.

Язык: Английский

Процитировано

2

Efficient Synthesis of Highly Fused Quinazolinone Derivatives via Multiple C−C Bond Formations and 1,4‐Palladium Migration DOI
Sampath Thavaselvan, Natarajan Arumugam, Abdulrahman I. Almansour

и другие.

European Journal of Organic Chemistry, Год журнала: 2023, Номер 27(6)

Опубликована: Дек. 9, 2023

Abstract An efficient palladium‐catalyzed annulation of 3‐arylquinazolinones with mono and double alkyne insertion was developed for the synthesis fused quinazolinone derivatives in 43–80 % yields. A notable effect observed product yield, when bases/additives were modulated. The reaction mechanism is believed to proceed through C−X cleavage/alkyne insertion/1,4‐Pd migration C−H a one‐pot manner.

Язык: Английский

Процитировано

1

Rapid synthesis of benzofulvenes from α-bromodiarylethylenes based on a 1,4-palladium shift strategy DOI
Abdur Rahim,

Shuming Zhan,

Biqiong Hong

и другие.

Organic Chemistry Frontiers, Год журнала: 2023, Номер 11(4), С. 1225 - 1231

Опубликована: Дек. 29, 2023

The synthesis of benzofulvenes from α-halo diarylethylenes through 1,4-palladium migration has been reported. reaction accepts a variety functional groups and affords wide range functionalized up to 93% yields.

Язык: Английский

Процитировано

1

Palladium-catalyzed cascade cyclization of α,β-unsaturated N-tosylhydrazones with iodoarenes : access to 2H-chromenes and 2H-quinolines DOI

Yiyi Zheng,

Xi-Wei Zhu,

Yi-Yun Pan

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(46), С. 9121 - 9124

Опубликована: Янв. 1, 2024

A palladium-catalyzed cascade reaction of α,β-unsaturated N -tosylhydrazones with iodoarene derivatives containing a nucleophilic group is described.

Язык: Английский

Процитировано

0

Aryl‐to‐Vinyl 1,4‐Nickel Migration/Reductive Cross‐Coupling Reaction for the Stereoselective Synthesis of Multisubstituted Olefins DOI Open Access

Cui‐Tian Wang,

Peng‐Yu Liang,

Ming Li

и другие.

Angewandte Chemie, Год журнала: 2023, Номер 135(28)

Опубликована: Май 5, 2023

Abstract The aryl‐to‐vinyl nickel 1,4‐migration (1,4‐Ni migration) reaction has been reported for the first time. generated alkenyl Ni species undergo a reductive coupling with unactivated brominated alkanes affording series of trisubstituted olefins. This tandem exhibits mild conditions, broad substrate scope, high regioselectivity, and excellent Z / E stereoselectivity. A controlled experiments have shown that critical 1,4‐Ni migration process is reversible. In addition, intermediates obtained after are highly stereoselective do not isomerization. trace isomerization products caused by instability product.

Язык: Английский

Процитировано

0