Rh(III)-Catalyzed Dienylation and Cyclopropylation of 1,2,3-Benzotriazinones with Alkylidenecyclopropanes DOI
Yanzhi Liu, Yao‐Fu Zeng,

Jiaohang Wei

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(28), P. 5179 - 5184

Published: July 6, 2023

Rh (III)-catalyzed dienylation and cyclopropylation of 1,2,3-benzotriazinones with alkylidenecyclopropanes (ACPs) has been achieved. Different from the previous reports 1,2,3-benzotriazinones, triazinone ring remained intact in this C-H bond functionlization reaction. Also, denitrogenative could also be realized by changing reaction temperature. This protocol is featured high E selectivity, wide substrate scope, divergent structures products.

Language: Английский

Recent advances of visible-light photocatalysis in the functionalization of organic compounds DOI
Vishal Srivastava, Pravin K. Singh, Praveen P. Singh

et al.

Journal of Photochemistry and Photobiology C Photochemistry Reviews, Journal Year: 2022, Volume and Issue: 50, P. 100488 - 100488

Published: Feb. 2, 2022

Language: Английский

Citations

135
Rational Design of Co(II)‐Pyridine‐Decorated Reduced Phosphomolybdate Photocatalysts for Efficient Aniline Oxidation under Mild Conditions DOI
Xiaohui Liu, Hui Li, Na Xu

et al.

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: 42(23), P. 2970 - 2978

Published: Aug. 21, 2024

Comprehensive Summary The conversion of aniline to nitrosobenzene (NSB), a key step in the synthesis important chemicals, demands development environmentally friendly photocatalysts that operate under mild conditions. This process is driven by need for sustainable methods, given toxic nature and its central role production dyes, pharmaceuticals, agricultural chemicals. study reports on three reduced phosphomolybdate compounds with Co(II) centers polypyridine ligands, which show great potential as oxidation NSB. uses 30% H 2 O oxidant sole catalysts, achieving high rates selectivity without additional additives or photosensitizers. integration multidentate ligands {P 4 Mo 6 } clusters significantly reduces band gap, facilitating visible‐light‐driven photocatalysis. adsorption interaction between coordinated water molecules Co ions found enhance rate aniline, finding supported DFT analyses.

Language: Английский

Citations

10
CdS Quantum Dots for Metallaphotoredox-Enabled Cross-Electrophile Coupling of Aryl Halides with Alkyl Halides DOI
Julianna M. Mouat, Jonas K. Widness, Daniel G. Enny

et al.

ACS Catalysis, Journal Year: 2023, Volume and Issue: 13(13), P. 9018 - 9024

Published: June 22, 2023

Semiconductor quantum dots (QDs) offer many advantages as photocatalysts for synthetic photoredox catalysis, but no reports have explored the use of QDs with nickel catalysts C-C bond formation. We show here that 5.7 nm CdS are robust photoredox-promoted cross-electrophile coupling (40 000 TON). These conditions can be utilized on small scale (96-well plate) or adapted to flow. NMR studies triethanolamine (TEOA) capped active catalyst and TEOA displace native phosphonate carboxylate ligands, demonstrating importance QD surface chemistry.

Language: Английский

Citations

20
Divergent Reactivity of 1,2,3-Benzotriazin-4(3H)-ones: Photocatalytic Synthesis of 3-Substituted Isoindolinones Achieved through a Nitrogen-Mediated Hydrogen Atom Shift DOI
Fostino R. B. Bokosi, Oisin J. Shiels, Christopher Richardson

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(3), P. 1836 - 1845

Published: Jan. 16, 2024

A regioselective visible-light-mediated denitrogenative alkene insertion of 1,2,3-benzotriazin-4(3H)-ones was developed to access 3-substituted isoindolinones, an important structural motif present in many biologically active molecules and natural products. Notably, divergent reactivity achieved by switching from reported nickel catalysis (where C3-substituted 3,4-dihydroisoquinolin-1(2H)-ones form) photocatalysis, where photocatalytic denitrogenation a subsequent nitrogen-mediated hydrogen atom shift lead exclusive isoindolinone formation. The reaction is compatible with activated terminal alkenes cyclic α,β-unsaturated esters ketones, wide functional group tolerance for N-substitution the 1,2,3-benzotriazin-4(3H)-ones. utility this procedure highlighted gram-scale synthesis postsynthetic amidation. To understand origin unique product selectivity, experimental computational mechanistic studies were performed.

Language: Английский

Citations

7
Recent Advancement in the Conversion of 1,2,3‐Benzotriazin‐4(3H)‐One to Other Heterocyclic Systems and Their Applications: A Concise Review DOI Open Access
Zunera Khalid, Hafiz Adnan Ahmad, Munawar Ali Munawar

et al.

ChemistrySelect, Journal Year: 2025, Volume and Issue: 10(5)

Published: Feb. 1, 2025

Abstract The nitrogen containing 1,2,3‐benzotriazin‐4(3 H )‐one is structurally worthwhile system for its notable applications in the synthesis of N─ , O ─ and S─ heterocycles bears pivotal significant usage pharmaceutical industrial chemicals. Today most common items like dyes, cosmetics, sanitizers, insecticides plastics are based on heterocyclic moieties. Different starting materials used industrially formation diverse but a valuable structure to prepare numerous products. These conversions radiation or metal‐catalyzed denitrogenation annulation type reactions provide easy, one‐step atom‐economical route. vast significance their cheap make this subject interesting scientific researchers industrialists. This mini review summarizes recent developments transformation ring various other structures phenanthridinones, isoquinolones, coumarin‐1‐imines, benzamides, pyrroloquinazolinones, indolin‐1‐ones, 1,2‐benzisoselenazol‐3(2 )‐ones benzofuranones. Some emerging drugs ebselen, losartan, irbesartan, luotonin A, deoxyvasicinone mackinazolinone have been successfully synthesized from differently substituted benzotriazinones.

Language: Английский

Citations

1
Mechanoredox/Nickel Co-Catalyzed Cross Electrophile Coupling of Benzotriazinones with Alkyl (Pseudo)halides DOI
Huimin Wang,

Wenbin Ding,

Gang Zou

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(18), P. 12891 - 12901

Published: Aug. 24, 2023

An air-tolerant mechanoredox/nickel cocatalyzed cross electrophile coupling of benzotriazinones with alkyl (pseudo)halides is developed by liquid-assisting grinding in the presence manganese powders and strontium titanate as a reductant cocatalyst, respectively. Mechanical activation metal surfaces via ball milling eliminates chemical activator for manganese, while mechanoredox cocatalysis remarkably improves aryl/alkyl piezoelectricity-mediated radical generation from halides. Both display reactivities different those conventional thermal chemistry solution. The scope reaction demonstrated 26 examples, showing high chemoselectivity bromides vs chlorides.

Language: Английский

Citations

15
Recent Advances in the Application of P(III)-Nucleophiles to Create New P−C Bonds through Michaelis–Arbuzov-Type Rearrangement DOI
Biquan Xiong,

Minjing Yuan,

Chonghao Shi

et al.

Topics in Current Chemistry, Journal Year: 2024, Volume and Issue: 382(1)

Published: March 1, 2024

Language: Английский

Citations

6
Continuous Flow Synthesis of Benzotriazin-4(3H)-ones via Visible Light Mediated Nitrogen-Centered Norrish Reaction DOI Creative Commons
Jorge García‐Lacuna, Marcus Baumann

Organic Letters, Journal Year: 2024, Volume and Issue: 26(12), P. 2371 - 2375

Published: March 11, 2024

We report a new protocol for the synthesis of substituted benzotriazin-4(3H)-ones which are underrepresented heterocyclic scaffolds with important pharmacological properties. Our method exploits acyclic aryl triazine precursors that undergo photocyclization reaction upon exposure to violet light (420 nm). Continuous flow reactor technology is exploited afford excellent yields in only 10 min residence time no additives or photocatalysts needed. The underlying mechanism appears be based on an unprecedented variation classical Norrish type II concomitant fragmentation and formation N–N bonds. Scalability, process robustness, green credentials this intriguing transformation highlighted.

Language: Английский

Citations

6
Improved Palladium Catalysis in Suzuki‐Type Coupling of Benzotriazinones for o‐Aryl/Alkenyl Benzamides DOI
Minling Xü, Ke Xü, Gang Zou

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(11), P. 2623 - 2628

Published: April 20, 2024

Abstract A palladium catalyst system based on PdCl 2 (PPh 3 ) or (dppf) is reported for Suzuki‐type coupling of both N ‐aryl and alkyl benzotriazinones with aryl/alkenyl boronic acids to afford a series ortho ‐aryl/alkenyl benzamides in yields up 99%, showing improvements catalytic efficiency, substrate scope practicality. Scope limitations the improved protocol have been demonstrated more than 40 examples, including multigram‐scale synthesis activated o ‐biphenyl amide. Large electronic steric effects from acid counterpart observed, implying transmetallation boron should be involved rate‐determining step cycle.

Language: Английский

Citations

6
Photocatalytic C–P bond formation based on the reaction of carbon-centered radicals with phosphides DOI

Shiyi Zhao,

Yi-Yun Huang,

Shihao Deng

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(17), P. 4882 - 4894

Published: Jan. 1, 2024

This review focuses on the synthesis of C–P bonds using carbon-centered radicals with phosphorous compounds different valence states (P III , P V 4 ) under photocatalysis.

Language: Английский

Citations

6