Nickel‐Catalyzed Regioselective Intermolecular Dialkylation of Alkenylarenes: Generation of Two Vicinal C(sp3)−C(sp3) Bonds Across Alkenes** DOI Creative Commons

Daniel M. Lux,

Vivek Aryal,

Doleshwar Niroula

et al.

Angewandte Chemie, Journal Year: 2023, Volume and Issue: 135(32)

Published: June 15, 2023

Abstract We disclose a Ni‐catalyzed regioselective dialkylation reaction of alkenylarenes with α‐halocarbonyls and alkylzinc reagents. The produces γ‐arylated alkanecarbonyl compounds the generation two new C(sp 3 )−C(sp ) bonds at vicinal carbons alkenes. This is effective for use primary, secondary tertiary α‐halocarboxylic esters, amides ketones in conjunction primary reagents as sources terminal cyclic internal

Language: Английский

Visible-Light-Induced Redox-Neutral Difunctionalization of Alkenes and Alkynes DOI
Susmita Mondal, Sumit Ghosh, Alakananda Hajra

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(72), P. 9659 - 9691

Published: Jan. 1, 2024

The twelve principles of green chemistry illuminate the pathway in direction sustainable and eco-friendly synthesis, marking a fundamental shift synthetic organic paradigms. In this realm, harnessing power visible light for difunctionalization various skeletons without employing any external oxidant or reductant, specifically termed as redox-neutral difunctionalization, has attracted tremendous interest from chemists due to its low cost, easy availability environmentally friendly nature contrast traditional metal-catalyzed difunctionalizations. This review presents an overview recent updates on visible-light-induced reactions with literature coverage up May 2024.

Language: Английский

Citations

11

Decatungstate‐Photocatalyzed Diastereoselective Dearomative Hydroalkylation of Indoles DOI Creative Commons

Emeric Montinho‐Inacio,

Damien Bouchet, Wei‐Yang Ma

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(22)

Published: April 16, 2024

Abstract In this study, we present an efficient and straightforward dearomative hydroalkylation of indoles. By utilizing alkanes or ethers as alkyl radical sources employing TBADT a cost‐effective photocatalyst for direct hydrogen atom transfers (HAT), achieved successful conversion these heterocyclic derivatives into 2‐alkylindolines with good to excellent yields high diastereoselectivity under mild reaction conditions.

Language: Английский

Citations

8

Asymmetric synthesis of unnatural α-amino acids through photoredox-mediated C–O bond activation of aliphatic alcohols DOI Creative Commons
Gregory R. Alvey, Elena V. Stepanova, Andrey Shatskiy

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: 15(19), P. 7316 - 7323

Published: Jan. 1, 2024

A practical protocol for the stereoselective synthesis of unnatural α-amino acids is disclosed, using ubiquitous aliphatic alcohols as radical precursors to form acid backbone under redox-neutral photoredox-mediated conditions.

Language: Английский

Citations

6

Nickel‐Catalyzed Regioselective Intermolecular Dialkylation of Alkenylarenes: Generation of Two Vicinal C(sp3)−C(sp3) Bonds Across Alkenes** DOI Creative Commons

Daniel M. Lux,

Vivek Aryal,

Doleshwar Niroula

et al.

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(32)

Published: June 15, 2023

We disclose a Ni-catalyzed regioselective dialkylation reaction of alkenylarenes with α-halocarbonyls and alkylzinc reagents. The produces γ-arylated alkanecarbonyl compounds the generation two new C(sp

Language: Английский

Citations

16

Synergistic Brønsted Base/Photoredox‐Catalyzed Three‐Component Coupling with Malonates to Synthesize δ‐Hydroxy Esters and δ‐Keto Esters DOI
Ting Li, Wei Wang, Ming Dong

et al.

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: 42(9), P. 957 - 962

Published: Jan. 18, 2024

Comprehensive Summary Multicomponent alkene 1,2‐dicarbofunctionalizations (DCFs) have emerged as a powerful strategy to rapidly incorporate both two carbon subunits across one C—C double bond in step for enhancing molecular complexity and diversity. To the best of our knowledge, there is only report on photoredox‐catalyzed three‐component DCFs with malonates through radical−radical cross‐coupling, while radical‐polar crossover (RPC)‐type were still rare. Herein, we describe redox‐neutral RPC‐type 1,2‐dialkylation styrenes aldehydes synergistic Brønsted base/photoredox catalysis system. This transition‐metal‐free provides an efficient clean approach broad variety δ‐hydroxy esters also features exceptionally mild conditions, wide compatibility substrate scope functional groups, high atomic economy. Moreover, 1,2‐alkylacylation from same starting materials was achieved one‐pot manner such coupling subsequent two‐electron oxidation process, providing set δ‐keto interest pharmaceutical research.

Language: Английский

Citations

5

N-Heterocyclic nitrenium-catalyzed triple domino reaction of organic iodides for the synthesis of phthalides and δ-lactones DOI Creative Commons
Xin Wang, Sixian Wang, Weige Zhang

et al.

Green Synthesis and Catalysis, Journal Year: 2025, Volume and Issue: unknown

Published: April 1, 2025

Language: Английский

Citations

0

N-Heterocyclic nitrenium-catalyzed photoreductive radical-polar crossover for alkene dicarbofunctionalization DOI Creative Commons

Youfeng Han,

Beibei Zhang, Zhixiang Wang

et al.

Green Synthesis and Catalysis, Journal Year: 2024, Volume and Issue: unknown

Published: March 1, 2024

The photoredox radical-polar crossover paradigm is a valuable tool for 1,2-difunctionalization of alkenes. However, the use unactivated alkyl halides as radical precursors remains far less developed. Here, we report photoreductive N-heterocyclic nitrenium-catalyzed 1,2-dicarbofunctionalization alkenes by using and aryl iodides. These reactions can be carried out under simple, transition-metal-free conditions with easily obtainable materials such alkyl/aryl halides, alkenes, aldehydes. exhibit broad range substrate compatibility good tolerance towards functional groups. This approach offers new to unlock carbon skeletons.

Language: Английский

Citations

3

Harnessing Bromo/Acyloxy Transposition (BrAcT) and Excited-State Copper Catalysis for Styrene Difunctionalization DOI
Upasana Mukherjee, Jagrut Shah, Djamaladdin G. Musaev

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(31), P. 21271 - 21279

Published: July 23, 2024

1,2-Difunctionalization of styrenes, adding two distinct functional groups across the C═C double bond, has emerged as a powerful tool for enhancing molecular complexity. Herein, we report development regioconvergent β-acyloxylation-α-ketonylation styrenes through bromo/acyloxy transposition (BrAcT) and excited-state copper catalysis. This approach is amenable to gram-scale synthesis tolerates wide range complex frameworks, including derivatives natural products marketed drugs. Our experimental computational studies suggest unique mechanism featuring dynamic, ionic BrAcT process copper-catalyzed redox reactions. We anticipate that this could serve broadly applicable versatile strategy β-acyloxylation-α-functionalization creating valuable intermediates preparing new pharmaceuticals, agrochemicals, materials.

Language: Английский

Citations

3

Cu-catalyzed alkylarylation of alkenes via N-directed remote C(sp3)–H functionalization DOI
Rong Rui, Bin Wang,

Xiaojing Xu

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(5), P. 1484 - 1489

Published: Jan. 1, 2024

Herein, we report a copper-catalyzed alkylarylation reaction of alkenes using N -fluoroamides and arylboronic acids.

Language: Английский

Citations

2

Recent Progress in Radical Involved Alkene Dialkylation DOI

Lingyi Lu,

Xiaodong Qiu

Chinese Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 44(6), P. 1701 - 1701

Published: Jan. 1, 2024

Language: Английский

Citations

2