Photocatalytic [2+2+m] Cyclization of 2‐Cyanoaryl Acrylamides with 2‐Bromocarbonyls Involving C(sp3)−H Functionalization DOI
Chuan Liu,

Guangpeng Yan,

Zonglang Wu

et al.

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(24), P. 4513 - 4519

Published: Oct. 31, 2023

Abstract An oxidant‐free photocatalytic [2+2+m] cyclization of 2‐cyanoaryl acrylamides with 2‐bromocarbonyls is reported, enabling the assembly biologically important N‐heterocycle‐fused quinolinones including benzo[1,6]naphthyridinones and pyrrolo[3,2‐ c ]‐quinolines. This protocol proceeds through a radical relay pathway alkene difunctionalization along an intramolecular cyano insertion subsequent site‐specific functionalization inert C( sp 3 )−H bond enabled by cyano‐derived iminyl radical‐mediated 1,n‐hydrogen atom transfer. Notably, this transformation selectively formed two distinct C−C bonds, one C−N bond, quaternary carbon center in one‐pot procedure.

Language: Английский

Arylthianthrenium Salts as the Aryl Sources: Visible Light/Copper Catalysis-Enabled Intermolecular Azidosulfonylation of Alkenes DOI
Hao Xu, Xufeng Li, Yifei Wang

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(9), P. 1845 - 1850

Published: Feb. 26, 2024

The difunctionalization of alkenes using aryl thianthrenium salts as the sources has been reported sporadically. However, four-component on basis not thus far and still remains a challenge. Herein, visible light/copper catalysis-enabled reaction salts, DABCO·(SO

Language: Английский

Citations

23

Photoredox streamlines electrocatalysis: photoelectrosynthesis of polycyclic pyrimidin-4-ones through carbocyclization of unactivated alkenes with malonates DOI

Minglin Tao,

Feng Qin,

Kaixing Gong

et al.

Green Chemistry, Journal Year: 2024, Volume and Issue: 26(7), P. 4199 - 4208

Published: Jan. 1, 2024

A new photoelectrocatalytic mode permits the synthesis of polycyclic pyrimidin-4-ones through dehydrogenative cyclization malonates with unactivated alkenes.

Language: Английский

Citations

15

Photoinduced radical-polar crossover cyclization reactions DOI
Zhiming Zhu, Yongxin Zhang, Ziyang Li

et al.

Chem Catalysis, Journal Year: 2024, Volume and Issue: 4(5), P. 100945 - 100945

Published: March 5, 2024

Language: Английский

Citations

13

Visible light/copper catalysis enabled Heck-like coupling between alkenes and cyclic sulfonium salts via selective C–S bond cleavage DOI

Xianqin Liu,

Xufeng Li, Linyuan Wang

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(8), P. 2195 - 2200

Published: Jan. 1, 2024

A Heck-like coupling of cyclic sulfonium salts with alkenes via selective C–S bond cleavage using a copper complex as photosensitizer through visible-light-driven redox-neutral process has been developed.

Language: Английский

Citations

9

Direct C–H Alkylation of Benzothiadiazoles via Organic Photoredox Catalysis DOI

Guiqing Xu,

Jiayuan Lv,

Qingjie Ding

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(4), P. 2777 - 2781

Published: Feb. 5, 2024

2,1,3-Benzothiadiazole is widely used as a privileged scaffold in pharmaceuticals and organic functional materials. Nonetheless, many current methods for the functionalization of 2,1,3-benzothiadiazole rely on preactivation, transition metal catalysts/promoters, or an elevated reaction temperature. Herein we disclose transition-metal-free visible-light-induced photocatalytic method direct C–H alkylation using readily accessible carboxylic acid derivatives, i.e., N-hydroxyphthalimide esters (NHPEs), alkylating reagents under room This mild scalable highlighted by late-stage installation benzothiadiazole drugs natural products.

Language: Английский

Citations

8

Electrochemical Sulfonylation/Cyclization of N-Alkenylacrylamides with Sodium Sulfinates or Sulfonyl Hydrazides DOI
Zhixian Yang,

Lu-Cai Ding,

Gui-Hong Yang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(15), P. 10660 - 10677

Published: July 18, 2024

Two general protocols for the regioselective electrochemically enabled sulfonylation cyclization of

Language: Английский

Citations

8

Recent Advances in the Functionalization of Remote C−H Bonds by Hofmann‐Löffler‐Freytag‐type Reactions DOI

Xiaoxu Teng,

Tingting Yu, Jianwei Shi

et al.

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(19), P. 3211 - 3226

Published: Aug. 26, 2023

Abstract Nitrogen radicals are one of the most useful reactive intermediates for selective transposition via intramolecular hydrogen atom transfer (HAT). The Hofmann‐Löffler‐Freytag (HLF) reaction is a distinctive radical‐based approach in which nitrogen used remote C−H bond functionalization HAT. Due to its excellent regioselectivity and atomic economy, HLF represents new preparation valuable functional molecules. In this review, we provide brief overview recent research advances mediated HLF‐type reactions involving intermolecular cyclization, δ ‐site functionalization.

Language: Английский

Citations

19

Synthesis of Heptacyclic Compounds through C–H Bond Activation-Initiated Cascade Reactions DOI
Xing He,

Kangli Liu,

Shengnan Yan

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(35), P. 7425 - 7430

Published: Aug. 22, 2024

Presented herein is an atom- and step-economical method enabling the precise assembly of a heptacyclic scaffold containing both azocine indoline units through cascade reactions indolin-1-yl(aryl)methanimines with diazo indanediones. The formation products involves C–H bond activation double carbene insertion followed by intramolecular condensation, retro-[2 + 2] cycloaddition, recyclization. This reaction not only provided concise straightforward strategy for synthesis otherwise difficult to obtain compounds from readily available substrates but also disclosed unprecedented mode derivatives compounds. In general, this novel synthetic protocol has advantages, such as easily obtainable substrates, structurally sophisticated products, procedure, good compatibility diverse functional groups, ready scalability. Moreover, thus obtained showed decent antiproliferative activity against three human cancer cell lines.

Language: Английский

Citations

7

Chemoselective electrochemical seleno-cyclization of dienes to medium-sized benzo[b]azocines DOI

Zhichuan Wang,

Xin Wang, Q. Li

et al.

Chinese Chemical Letters, Journal Year: 2023, Volume and Issue: 35(2), P. 109058 - 109058

Published: Sept. 10, 2023

Language: Английский

Citations

15

Deep eutectic solvents as sustainable media for multicomponent sulfonylation: an efficient strategy to synthesize (hetero)aryl sulfones DOI
Haibo Zhu, Yangbo Zhong,

Liyuan Yan

et al.

Green Chemistry, Journal Year: 2024, Volume and Issue: 26(3), P. 1387 - 1392

Published: Jan. 1, 2024

A green and sustainable multicomponent sulfonylation starting from boronic acids, K 2 S O 5 halides has been developed using a deep eutectic solvent (DES) as reaction medium.

Language: Английский

Citations

5