Molecular Catalysis, Journal Year: 2023, Volume and Issue: 547, P. 113291 - 113291
Published: June 12, 2023
Language: Английский
Chemical Reviews, Journal Year: 2024, Volume and Issue: unknown
Published: Nov. 26, 2024
Cross-electrophile coupling (XEC), defined by us as the cross-coupling of two different σ-electrophiles that is driven catalyst reduction, has seen rapid progression in recent years. As such, this review aims to summarize field from its beginnings up until mid-2023 and provide comprehensive coverage on synthetic methods current state mechanistic understanding. Chapters are split type bond formed, which include C(sp
Language: Английский
Citations
24
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
Molecules, Journal Year: 2025, Volume and Issue: 30(5), P. 1060 - 1060
Published: Feb. 26, 2025
An efficient and air-tolerant Ni-catalyzed denitrogenative cross-electrophile coupling of benzotriazinones with benzyl chlorides has been developed via liquid-assisted grinding by using Mn powders as reductant DMF assisting liquid in the presence anhydrous calcium chloride. Scope limitations protocol to access diarylmethanes have demonstrated more than 20 examples, showing acceptable tolerance functional group steric hindrance. Although electron-withdrawing substituents on benzotriazinone or counterparts decrease yields significantly, a series N-alkyl-2-benzylbenzamides, bearing an ortho-carbamoyl aryl group, could be obtained modest good yields.
Language: Английский
Citations
1
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
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
The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(24), P. 16567 - 16577
Published: Dec. 1, 2022
The nickel-catalyzed cross-electrophile coupling of 1,2,3-benzotriazin-4(3H)-ones with aryl bromides to generate a diverse array ortho-arylated benzamide derivatives has been developed. reaction displayed good functional group tolerance Zn as the reductant. key this transformation is ring opening benzotriazinones, which undergo denitrogenative process obtain various (29 examples, 42-93% yield). scalability was demonstrated.
Language: Английский
Citations
21
Organic Letters, Journal Year: 2022, Volume and Issue: 24(49), P. 9012 - 9016
Published: Dec. 5, 2022
An expedient synthesis of benzo[c][1,2]dithiol-3-ones via metal-free denitrogenative transannulation benzotriazinones is developed, which represents the first example acid-mediated heteroannulation benzotriazinones. This newly discovered reactivity enables streamline diverse in decent yields by using sodium sulfide as sulfur source under simple reaction conditions.
Language: Английский
Citations
20
Chemical Communications, Journal Year: 2024, Volume and Issue: 60(26), P. 3571 - 3574
Published: Jan. 1, 2024
Herein, a novel Pd-catalyzed denitrogenation/vinylation of benzotriazinones using vinylene carbonate as the vinylation reagent is reported. This transformation demonstrates an unprecedented skeletal editing approach, effectively converting NN to CC fragments
Language: Английский
Citations
5
Organic Letters, Journal Year: 2023, Volume and Issue: 25(29), P. 5443 - 5447
Published: July 13, 2023
We herein developed a palladium-catalyzed reaction of [1,2,3]-benzotriazin-4(3H)-ones with DABAL-Me3 [bis(trimethylaluminum)-1,4-diazabicyclo[2.2.2]octane adduct], cheap, stable, and solid organoaluminum reagent. In the presence Pd(OAc)2/XantPhos as commercially available catalyst, underwent denitrogenative coupling to afford wide array N-aryl amides derived from ortho-methylated carboxylic acids. Under same catalytic conditions, ortho-ethylation could also be achieved by using triethylaluminum.
Language: Английский
Citations
11
Journal of Organometallic Chemistry, Journal Year: 2024, Volume and Issue: 1013, P. 123156 - 123156
Published: April 25, 2024
Language: Английский
Citations
4