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

et al.

Angewandte Chemie, Journal Year: 2023, Volume and Issue: 135(28)

Published: May 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.

Language: Английский

The Carbene Chemistry of N-Sulfonyl Hydrazones: The Past, Present, and Future DOI
Xiaolong Zhang, Paramasivam Sivaguru,

Yongzhen Pan

et al.

Chemical Reviews, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 10, 2025

N-Sulfonyl hydrazones have been extensively used as operationally safe carbene precursors in modern organic synthesis due to their ready availability, facile functionalization, and environmental benignity. Over the past two decades, there has tremendous progress chemistry of N-sulfonyl presence transition metal catalysts, under metal-free conditions, or using photocatalysts photoirradiation conditions. Many transfer reactions are unique cannot be achieved by any alternative methods. The discovery novel development highly enantioselective new skeletal editing represent notable recent achievements hydrazones. This review describes overall made hydrazones, organized based on reaction types, spotlighting current state-of-the-art remaining challenges addressed future. Special emphasis is devoted identifying, describing, comparing scope limitations methodologies, key mechanistic scenarios, potential applications complex molecules.

Language: Английский

Citations

6

1,3-diene-based AIEgens: Stereoselective synthesis and applications DOI Creative Commons

Xiao‐Mei Nong,

Ao Gu,

Shuyang Zhai

et al.

iScience, Journal Year: 2024, Volume and Issue: 27(3), P. 109223 - 109223

Published: Feb. 15, 2024

SummaryIn recent years, significant advancements have been made in the synthesis and application of 1,3-dienes. This specific structural motif has garnered attention from researchers materials science biology due to its unique aggregation-induced emission (AIE) properties extensive conjugation systems. The luminescent characteristics these compounds are notably influenced by geometry two double bonds. Therefore, it is essential consolidate stereoselective synthetic strategies for comprehensive review seeks elucidate diverse techniques employed attain stereo-control 1,3-diene-based AIE luminogens (AIEgens). Particular emphasis placed on comprehending determinants stereoselectivity exploring array substrates amenable methods. Furthermore, underscores exhibited their utility organic light-emitting diodes (OLEDs), stimuli-responsive materials, sensors, bioimaging, photodynamic therapy (PDT).Graphical abstract

Language: Английский

Citations

7

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

Cui‐Tian Wang,

Peng‐Yu Liang,

Ming Li

et al.

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(28)

Published: May 5, 2023

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.

Language: Английский

Citations

17

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

Palladium-catalyzed intermolecular formal [3+2] cyclization/C-H alkylation of polyfluoroarenes DOI
Zhongyao Jiang, Chenglin Liu,

Mingxia Wu

et al.

Chemical Communications, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

A sequential three-component intermolecular carbopalladation/Heck cyclization/intermolecular C–H bond functionalization for versatile alkylated polyfluoroarenes containing an indene skeleton is presented.

Language: Английский

Citations

0

Synthesis of benzoheterocycles by palladium-catalyzed migratory cyclization through an unexpected reaction cascade DOI Creative Commons
Wencong Li, Lin Zhang,

Shiming Bai

et al.

Nature Communications, Journal Year: 2025, Volume and Issue: 16(1)

Published: April 9, 2025

Migratory functionalization of C-H bonds through metal migration from carbon to under transition catalysis is a process significant academic and industrial interest. Herein, palladium-catalyzed migratory cyclization α-bromoalkene derivatives ArXCBr=CH2, in which X denotes phosphorus (P(O)R), silicon (SiR2), sulfur (SO2), (C(O)), nitrogen (NTs), or oxygen-based moiety, affording various benzoheterocyclic compounds has been developed. Mechanistic investigations have demonstrated that the reaction proceeds an unexpected cascade, with trans-1,2-palladium between sp2 carbons being key step catalytic cycle. To best our knowledge, this type not reported previously.

Language: Английский

Citations

0

Highly regioselective C–H carbonylation of alkenes with phenyl formateviaaryl to vinyl 1,4-palladium migration DOI
Ye Tao, Fangyuan Cheng, Jian Zhang

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(6), P. 1537 - 1543

Published: Jan. 1, 2023

A novel approach to synthesize β,β-diaryl substituted α,β-unsaturated esters in high efficiency and with excellent regio- stereoselectivities was developed.

Language: Английский

Citations

9

Stereoselective Synthesis of Conjugated Dienes via Aryl-to-Vinyl 1,4-Nickel Migration and Reductive Cross-Coupling DOI
Guohua Ren,

Haochen Li,

Yiming Duan

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 3, 2025

Selective functionalization of remote C-H bonds via metal/hydride shift and cross-coupling represents a powerful strategy in modern synthetic chemistry. Herein, we report highly efficient aryl-to-vinyl 1,4-nickel migration coupled with reductive for the stereoselective synthesis conjugated dienes. This tandem process proceeds under mild conditions, accommodates wide range substrates, achieves excellent regioselectivity Z/E stereoselectivity, offering valuable method constructing multisubstituted

Language: Английский

Citations

0

Palladium‐Catalyzed Carbonylation of ortho‐Alkenyl Iodobenzenes for the Construction of 3‐Arylindenones DOI Open Access
Min Qian, Lingyun Yao, Zhi Li

et al.

Chinese Journal of Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 14, 2025

Comprehensive Summary We developed a novel Pd‐catalyzed carbonylation of ortho ‐alkenyl iodobenzenes with CO, affording diverse array 3‐arylindenones in good to excellent yields (up 94% yield). This methodology exhibits broad substrate scope and functional group compatibility. The synthetic utility was demonstrated by gram‐scale reaction, product derivatizations, the preparation an intermediate for PPARγ agonist.

Language: Английский

Citations

0

Palladium-catalyzed carbene C–H insertion reaction of non-activated arenes DOI
Shihaozhi Wang, Jiahui Shi,

Shan Xu

et al.

Chinese Chemical Letters, Journal Year: 2025, Volume and Issue: unknown, P. 111225 - 111225

Published: April 1, 2025

Language: Английский

Citations

0