Cyclic Sulfoximines as Methyl and Perdeuteromethyl Transfer Agents and Their Applications in Photoredox Catalysis DOI Creative Commons
Peng Wu,

Gabriel Goujon,

Shulei Pan

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(51)

Published: Sept. 5, 2024

Benzo[1,3,2]dithiazole-1,1,3-trioxides are bench-stable and easy-to-use reagents. In photoredox catalysis, they generate methyl perdeuteromethyl radicals which can add to a variety of radical acceptors, including olefins, acrylamides, quinoxalinones, isocyanides, enol silanes, N-Ts acrylamide. As byproduct, salt is formed be regenerated the original methylating agent. Flow chemistry provides an option for reaction scale-up further underscoring synthetic usefulness these methylation Mechanistic investigations suggest single-electron transfer (SET) pathway induced by catalysis.

Language: Английский

Cobaloximes: selective nitrite reduction catalysts for tandem ammonia synthesis DOI
Shu‐Lin Meng, Chen Zhang, Chen Ye

et al.

Energy & Environmental Science, Journal Year: 2023, Volume and Issue: 16(4), P. 1590 - 1596

Published: Jan. 1, 2023

Herein, we demonstrate cobaloximes as a bioinspired molecular platform for exclusive ammonia synthesis via electrocatalytic NO 2 − reduction (eNO RR), which attained 98.5% faradaic efficiency (FE) under close-to-neutral conditions.

Language: Английский

Citations

47

Photocatalytic Umpolung Strategy for the Synthesis of α-Amino Phosphine Oxides and Deuterated Derivatives DOI
Chunhua Ma, Xiaofeng Li,

Xiya Chen

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(44), P. 8016 - 8021

Published: Oct. 30, 2023

Direct, economical, and green synthesis of deuterated α-amino phosphine oxides remains an elusive challenge in synthetic chemistry. Herein, we report a visible-light-driven umpolung strategy for synthesizing from isocyanide using 1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene as the photocatalyst D2O deuterium source. Moreover, streamlined sustainable methodology can be applied modification amino acids, natural products, drugs. The strong antiproliferative activity desired products indicates that method could provide novel privileged scaffold antitumor drug development.

Language: Английский

Citations

29

Synthetic Methods for Azaheterocyclic Phosphonates and Their Biological Activity: An Update 2004–2024 DOI
Martha C. Mayorquín‐Torres, Andreas Simoens, Eli Bonneure

et al.

Chemical Reviews, Journal Year: 2024, Volume and Issue: 124(12), P. 7907 - 7975

Published: May 29, 2024

The increasing importance of azaheterocyclic phosphonates in the agrochemical, synthetic, and medicinal field has provoked an intense search development synthetic routes for obtaining novel members this family compounds. This updated review covers methodologies established since 2004, focusing on synthesis phosphonates, which phosphonate moiety is directly substituted onto to structure. Emphasizing recent advances, classifies newly developed approaches according ring size providing information biological activities whenever available. Furthermore, summarizes various methods formation C–P bonds, examining sustainable such as Michaelis–Arbuzov reaction, Michaelis–Becker Pudovik Hirao coupling, Kabachnik–Fields reaction. After analyzing applications investigated years, a predominant focus evaluation these compounds anticancer agents evident. emerging underline versatility potential compounds, highlighting need continued research expand interesting family.

Language: Английский

Citations

14

Biomimetic Photoexcited Cobaloxime Catalysis in Organic Synthesis DOI Creative Commons
Phong Dam, Kaiming Zuo, Luis Miguel Azofra

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(33)

Published: May 22, 2024

Abstract Drawing inspiration from nature has long been a cornerstone of chemical innovation, with natural systems offering wealth untapped potential for discovery. In this minireview, we delve into the burgeoning field cobaloxime catalysis in organic synthesis, which mimics catalytic activity organometallic alkylcobalamine enzymes. Our focus lies on elucidating latest advancements area, as well delineating primary mechanistic pathways at play. By describing, and comparing these mechanisms, provide comprehensive overview current state‐of‐the‐art, while also shedding light key unresolved challenges that await further exploration.

Language: Английский

Citations

11

Manganese/Cobalt Bimetallic Relay Catalysis for Divergent Dehydrogenative Difluoroalkylation of Alkenes DOI
Zhong Tao,

Chengyihan Gu,

Yuhang Li

et al.

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(42)

Published: Aug. 29, 2023

The involvement of manganese radical for halogen atom transfer (XAT) reactions has been esteemed as one reliable method but encountered with limited catalytic models. In this paper, a novel bimetallic relay catalysis Mn2 (CO)10 and cobaloxime developed divergent dehydrogenative difluoroalkylation alkenes using commercially available difluoroalkyl bromides. A wide range structurally diverse terminal, cyclic internal well tetrasubstituted are found to be good coupling partners deliver difluoroalkylated allylic products difluoromethylated products, accompanied the production H2 by-product. This strategy features broad substrate scope, mild reaction conditions excellent functional group compatibility. Its success represents an important step-forward expedite construction rich library products.

Language: Английский

Citations

21

N-Allylation of Azoles with Hydrogen Evolution Enabled by Visible-Light Photocatalysis DOI

Chang-Ming You,

Cheng Huang, Sheng Tang

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(10), P. 1722 - 1726

Published: March 4, 2023

Direct N-allylation of azoles with hydrogen evolution has been achieved through the synergistic combination organic photocatalysis and cobalt catalysis. The protocol bypasses stoichiometric oxidants prefunctionalization alkenes produces (H2) as byproduct. This transformation highlights high step- atom-economy, efficiency, broad functional group tolerance for further derivatization, which opens a door C-N bond formation that is valuable in heterocyclic chemistry.

Language: Английский

Citations

19

Visible-Light-Induced Highly Site-Selective Direct C–H Phosphorylation of Pyrrolo[2,3-d]pyrimidine Derivatives with H-Phosphine Oxides DOI
Zhuo Zhang, Mingrui Liu, Min Liu

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(5), P. 2996 - 3009

Published: Feb. 15, 2024

An efficient and highly regioselective C6-phosphorylation protocol for pyrrolo[2,3-d]pyrimidine (7-DAP) derivatives with various H-phosphine oxides induced by visible light at room temperature is described the first time. This has been successfully achieved combination of Na2-eosin Y as a photocatalyst LPO an oxidant under transition metal- additive-free conditions. The broad substrate scope, good functional group tolerance, excellent regioselectivity, air tolerant conditions make this process favorable modification scaffold enrich phosphorylated 7-DAP compounds further biological evaluation.

Language: Английский

Citations

7

Visible-Light-Induced Annulation of Iodonium Ylides and 2-Isocyanobiaryls to Access 6-Arylated Phenanthridines DOI
Jinyang Chen, Hongyu Wu,

Hai‐Yang Song

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(13), P. 8360 - 8368

Published: June 1, 2023

A 1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene (4-CzIPN)-photocatalyzed cascade arylation/cyclization reaction of 2-isocyanobiaryls and iodonium ylides was established for the synthesis 6-arylated phenanthridines. This is first example employing as aryl radical sources in a visible-light-induced cyclization reaction.

Language: Английский

Citations

14

Photocatalytic cyclization of 3-(2-isocyanophenyl)quinazolin-4(3H)-ones for the construction of quinoxalino[2,1-b]quinazolinones DOI

Xian Wu,

Ling-Li Liu,

Chengli Xiang

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(18), P. 2556 - 2559

Published: Jan. 1, 2024

3-(2-Isocyanophenyl)quinazolin-4(3 H )-ones were designed and synthesized as new building units for the construction of novel quinoxalino[2,1- b ]quinazolinones under mild, photocatalytic metal-free conditions.

Language: Английский

Citations

5

Photo-induced phosphorylation/cyclization of N-homoallyl and N-allyl aldehyde hydrazones to access phosphorylated tetrahydropyridazines and dihydropyrazoles DOI

Ling-Li Liu,

Yechun Wu,

Chengli Xiang

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(35), P. 4687 - 4690

Published: Jan. 1, 2024

A visible-light-induced carbophosphorylation/cyclization of N -homoallyl and -allyl aldehyde hydrazones with phosphine oxides was developed to obtain phosphorylated tetrahydropyridazines dihydropyrazoles.

Language: Английский

Citations

5