Visible light-promoted transition metal-free direct C3-carbamoylation of 2H-Indazoles DOI Creative Commons
Chunhua Ma,

Linchun Shang,

Hanying Zhao

et al.

Frontiers in Chemistry, Journal Year: 2022, Volume and Issue: 10

Published: Nov. 29, 2022

We reported a general transition metal-free transformation to access C3-carbamoylated 2H-indazoles via visible light-induced oxidative decarboxylation coupling, in the presence of oxamic acids as coupling sources, 4CzIPN photocatalyst, and Cs2CO3 base. The great application potential this mild condition is highlighted by late-stage modification drugs, N-terminal peptides, good antitumor activity novel desired product.

Language: Английский

Alkyl radicals from diacyl peroxides: metal-/base-/additive-free photocatalytic alkylation of N-heteroaromatics DOI

Fukun Cheng,

Lulu Fan, Qi‐Yan Lv

et al.

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(20), P. 7971 - 7977

Published: Jan. 1, 2023

Alkyl diacyl peroxides were demonstrated to be efficient alkylating reagents for the visible-light-induced 4CzIPN-catalyzed direct C–H alkylation of N -heteroaromatics.

Language: Английский

Citations

47

Visible-light-induced four-component difunctionalization of alkenes to construct phosphorodithioate-containing quinoxalin-2(1H)-ones DOI
Xiao‐Ming Chen,

Lianhui Song,

Jun Pan

et al.

Chinese Chemical Letters, Journal Year: 2024, Volume and Issue: 35(11), P. 110112 - 110112

Published: June 25, 2024

Language: Английский

Citations

27

Decatungstate-photocatalyzed direct acylation of N-heterocycles with aldehydes DOI
Zhiyang Zhang,

Fukun Cheng,

Xinyu Ma

et al.

Green Chemistry, Journal Year: 2024, Volume and Issue: 26(12), P. 7331 - 7336

Published: Jan. 1, 2024

A novel photocatalytic acylation strategy was developed harnessing tetrabutylammonium decatungstate (TBADT) as a hydrogen atom transfer (HAT) photocatalyst to facilitate the direct coupling of aldehydes with N-heterocycles at ambient temperature.

Language: Английский

Citations

17

Recent advances in the photocatalytic synthesis of aldehydes DOI
Yi Wang, Xiaofei Liu, Wei‐Min He

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(16), P. 4198 - 4210

Published: Jan. 1, 2023

This review summarizes the recently developed photocatalytic strategies for installation of formyl group into various scaffolds.

Language: Английский

Citations

19

Hydrotrifluoroacetylation of Alkenes via Designer Masked Acyl Reagents DOI
Sangil Han, Kyra L. Samony,

Rifat N. Nabi

et al.

Journal of the American Chemical Society, Journal Year: 2023, Volume and Issue: 145(21), P. 11530 - 11536

Published: May 16, 2023

Because of its impressive ability to promote pharmaceutical activity, the introduction trifluoromethylacyl (CF3CO) functionality into organic compounds has become an important and growing research area. Although various protocols have been developed access trifluoroketones, use trifluoroacetyl radicals remains virtually undeveloped. Herein, we disclose a novel method for trifluoroacetylation through umpolung reagent, thereby transforming electrophilic radical nucleophilic radical. The applicability this transformation is highlighted by large-scale, late-stage reactions complex bioactive molecules sclareolide loratadine. Furthermore, direct trifluoromethyl ketones fluorinated analogues illustrates potential synthetic application our method.

Language: Английский

Citations

17

Visible Light Photoredox-Catalyzed Formyl/Carboxylation of Activated Alkenes with Glyoxylic Acid Acetals and CO2 DOI

Yang Han,

Yang Yao,

Qi Yang

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(20), P. 4194 - 4199

Published: May 15, 2024

A photoredox-catalyzed sequential α-formyl/carboxylation of alkenes with glyoxylic acid acetals and CO

Language: Английский

Citations

6

Visible-Light-Driven Transition-Metal-Free Site-Selective Access to Isonicotinamides DOI
Chunhua Ma, Yu Tian, Junyan Wang

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(45), P. 8265 - 8270

Published: Nov. 7, 2022

The greener synthesis of N-substituted isonicotinamides is high importance and remains a significant challenge to the chemistry community. Herein we delineated visible-light-driven, transition-metal-free, external-oxidant-free radical-radical cross-coupling reaction access via consecutive photoinduced electron transfer (ConPET). utility this protocol highlighted through N-terminal modification peptides late-stage drugs.

Language: Английский

Citations

28

4CzIPN-catalyzed radical-initiated cascade cyclization for the photosynthesis of polysubstituted quinolin-3-amines DOI

Shiqiang Mu,

Yu Guo,

Xiujuan Huang

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(13), P. 3259 - 3263

Published: Jan. 1, 2023

Substituted quinolin-3-amines are essential cores of many natural products and bioactive molecules.

Language: Английский

Citations

14

Dual iron- and organophotocatalyzed hydroformylation, hydroacylation and hydrocarboxylation of Michael-acceptors utilizing 1,3,5-trioxanes as C1-Synthone DOI Creative Commons

Viktor Klöpfer,

Anurag Chinchole, Oliver Reiser

et al.

Tetrahedron Chem, Journal Year: 2024, Volume and Issue: 10, P. 100073 - 100073

Published: April 16, 2024

A protocol based on photocatalytic cycles of both iron(III)chloride and 9,10-dicyanoanthracene (DCA) is developed for the masked hydroformylation, hydroacylation, hydrocarboxylation Michael-Acceptors utilizing readily available 1,3,5-trioxanes. Initiated by LMCT [FeCl4]– to generate chlorine radicals that promote hydrogen atom transfer (HAT) from trioxanes, used as co-photocatalyst accelerate formation desired products facilitating reoxidation iron(II) iron(III). The methodology robust, allowing generation aldehydes, ketones, carboxylic acids either altering trioxane deprotection strategy or subsequent photocatalyzed conversion initially obtained aldehydes.

Language: Английский

Citations

5

Photomediated Hydro(deutero)acylation of Olefins by Decarboxylative Addition of α-Oxocarboxylic Acids DOI

Fan Gao,

Zhi-Yu Liao,

Yu-Hang Ye

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(4), P. 2741 - 2747

Published: Feb. 1, 2024

Acyl radicals have been generated from the decarboxylation of α-oxocarboxylic acids by using a readily accessible organic pyrimidopteridine photoredox catalyst under ultraviolet-A (UV-A) light irradiation. These reactive acyl were smoothly added to olefins such as styrenes and diverse Michael acceptors, with assistance H2O/D2O hydrogen donors, enabling easy access range ketones/β-deuterio ketones. A wide are compatible this reaction, which shows reliable, atom-economical, eco-friendly protocol. Furthermore, postsynthetic diversifications applications presented.

Language: Английский

Citations

4