Cascade cyclization of alkene-tethered acylsilanes and allylic sulfones enabled by unproductive energy transfer photocatalysis DOI Creative Commons
Yunxiao Zhang, Yizhi Zhang, Chen Ye

et al.

Nature Communications, Journal Year: 2022, Volume and Issue: 13(1)

Published: Oct. 16, 2022

Abstract Developing photo-induced cascade cyclization of alkene-tethered acylsilanes is challenging, because are unstable under light irradiation. Herein, we report that the energy transfer from excited to a photocatalyst possesses lower triplet can inhibit undesired decomposition acylsilanes. With neutral Eosin Y as photocatalyst, an efficient synthesis cyclopentanol derivatives achieved with and allylic sulfones. The reaction shows broad substrate scope synthetic potential this transformation highlighted by construction which contain fused-ring or bridged-ring.

Language: Английский

Design principles of the use of alkynes in radical cascades DOI
Chaowei Hu,

Justice Mena,

Igor V. Alabugin

et al.

Nature Reviews Chemistry, Journal Year: 2023, Volume and Issue: 7(6), P. 405 - 423

Published: March 28, 2023

Language: Английский

Citations

53

Synthesis of Ester-Substituted Indolo[2,1-a]isoquinolines via Photocatalyzed Alkoxycarbonylation/Cyclization Reactions DOI
Jian-Qiang Chen,

Xiaodong Tu,

Binyan Qin

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(2), P. 642 - 647

Published: Jan. 5, 2022

A direct alkoxycarbonylation/cyclization reaction is accomplished under visible light-induced photoredox catalysis. With this approach, a variety of ester-substituted indolo[2,1-a]isoquinolines are prepared in good to excellent yields. It worth noting that method not only can afford the synthesis but also provide an alternative route for generating complex target structures bearing carboxylic esters.

Language: Английский

Citations

55

Electrophotocatalytic tri- or difluoromethylative cyclization of alkenes DOI
Danna Chen,

Xuege Yang,

Dongyin Wang

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(10), P. 2482 - 2490

Published: Jan. 1, 2023

Photoelectrocatalysis is mild yet potent and this work unlocks the potential of unactivated alkenes for oxidant-free oxidative cyclization alkenes.

Language: Английский

Citations

35

Photoredox catalysis harvesting multiple photon or electrochemical energies DOI Creative Commons
Mattia Lepori, Simon Schmid, Joshua P. Barham

et al.

Beilstein Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 19, P. 1055 - 1145

Published: July 28, 2023

Photoredox catalysis (PRC) is a cutting-edge frontier for single electron-transfer (SET) reactions, enabling the generation of reactive intermediates both oxidative and reductive processes via photon activation catalyst. Although this represents significant step towards chemoselective and, more generally, sustainable chemistry, its efficacy limited by energy visible light photons. Nowadays, excellent alternative conditions are available to overcome these limitations, harvesting two different but correlated concepts: use multi-photon such as consecutive photoinduced electron transfer (conPET) combination photo- electrochemistry in synthetic photoelectrochemistry (PEC). Herein, we review most recent contributions fields activations organic functional groups. New opportunities chemists captured, selective reactions employing super-oxidants super-reductants engage unactivated chemical feedstocks, scalability up gram scales continuous flow. This provides comparisons between techniques (multi-photon photoredox PEC) help reader fully understand their similarities, differences potential applications therefore choose which method appropriate given reaction, scale purpose project.

Language: Английский

Citations

30

Carbonylative transformation of aryl halides and strong bonds via cheap metal catalysts and sustainable technologies DOI Creative Commons
Maolin Yang, Yukun Liu, Xin Qi

et al.

Green Synthesis and Catalysis, Journal Year: 2024, Volume and Issue: 5(4), P. 211 - 269

Published: May 6, 2024

The development of catalytic carbonylation reactions has increased considerably. Although many reviews/chapters/books on have been published, summaries cheap metal-catalyzed aryl halides and other chemical bonds with high dissociation energy C-Y (Y = O, N, H) are still very rare. Focusing green sustainable chemistry, this review summarizes discusses the achievements carbonylative transformations (C(sp2)-X) strong based non-expensive metal catalysts (Co, Mn, Mo, Ni, Fe, Cu), photochemical electrochemical systems developed in recent decades.

Language: Английский

Citations

15

Photocatalytic Thio/Selenosulfonylation–Bicyclization of Indole-Tethered 1,6-Enynes Leading to Substituted Benzo[c]pyrrolo[1,2,3-lm]carbazoles DOI
Hang‐Dong Zuo, Xi Chen, Yue Zhang

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(18), P. 3828 - 3833

Published: April 29, 2024

The photocatalyzed radical-triggered thio/selenosulfonylation–bicyclization of indole-tethered 1,6-enynes has been established for the first time, enabling synthesis various previously unreported thio/selenosulfonylated benzo[c]pyrrolo[1,2,3-lm]carbazoles with moderate to good yields under mild conditions. reaction pathway was proposed, consisting energy transfer, homolytic cleavage, radical addition, 5-exo-dig, coupling, and a Mallory cascade. This approach exhibits wide substrate compatibility excellent tolerability toward functional groups is characterized by its remarkable efficiency in both bond formation annulation.

Language: Английский

Citations

13

Palladium‐Catalyzed Dual Csp2─Csp3 Bond Formation: A Versatile Platform for the Synthesis of Benzo‐Fused Heterocycles DOI Creative Commons
Jiahui Huang, Yang You,

Yijian Ma

et al.

Advanced Science, Journal Year: 2025, Volume and Issue: unknown

Published: April 28, 2025

Abstract Transition‐metal‐catalyzed transformations offer a powerful approach to rapidly synthesize complex benzo‐fused heterocycles, crucial for drug and material development. However, existing synthetic strategies face challenges such as limited functional group compatibility, reliance on ligands, difficulties in controlling chemoselectivity with prefunctionalized substrates. Herein, ligand‐free Pd(II)/Cu(I) catalytic system is presented that facilitates reactions between arylsulfonyl chlorides unactivated olefins under mild conditions, enabling the efficient synthesis of saturated six‐membered heterocycles. This streamlined strategy employs dual Csp 2 ─Csp 3 bond formation, producing diverse N/O‐polyheterocycles allowing late‐stage functionalization bioactive molecules excellent yields high chemoselectivity. The key success this reaction formation high‐valent Ar‐Pd(III) intermediate, which drives through 1,2‐Pd migration electrophilic C─H arylation. unique reactivity pathway heterocycles while effectively avoiding β‐H elimination typically associated Heck‐type reactions.

Language: Английский

Citations

1

Electrosynthesis of 1-indanones DOI

Jun Jiang,

Zheng Wang, Wei‐Min He

et al.

Chinese Chemical Letters, Journal Year: 2021, Volume and Issue: 32(5), P. 1591 - 1592

Published: March 6, 2021

Language: Английский

Citations

57

Recent advances in the synthesis of indolizine and its derivatives by radical cyclization/cross-coupling DOI

Jieru Hui,

Yan‐Long Ma,

Jiaji Zhao

et al.

Organic & Biomolecular Chemistry, Journal Year: 2021, Volume and Issue: 19(47), P. 10245 - 10258

Published: Jan. 1, 2021

The free-radical-induced syntheses of indolizines were reviewed by type catalyst.

Language: Английский

Citations

48

Iron‐Catalyzed Silylation and Spirocyclization of Biaryl‐Ynones: A Radical Cascade Process toward Silylated Spiro[5.5]trienones DOI
Fei Chen, Zheng Yang, Hao Yang

et al.

Advanced Synthesis & Catalysis, Journal Year: 2022, Volume and Issue: 364(9), P. 1537 - 1542

Published: March 11, 2022

Abstract Iron‐catalyzed cascade silyl radical addition/6‐ exo ‐trig cyclization/dearomatization of biaryl ynones has been developed. This approach uses silane as the precursor well silylation reagent, 1,10‐phenanthroline ligand, and tert ‐butyl hydroperoxide (TBHP) oxidant. By employing this tandem process, a series silylated spiro[5.5]trienones were prepared. magnified image

Language: Английский

Citations

32