Rhodium‐Catalyzed Oxidative Coupling of Potassium Vinyltrifluoroborate with Arenes: A Direct Access to Functionalized Styrene Derivatives DOI
Wenbo Ma, Yang Wang, Bo Li

et al.

Advanced Synthesis & Catalysis, Journal Year: 2022, Volume and Issue: 364(22), P. 3881 - 3887

Published: Oct. 6, 2022

Abstract Herein, we report a Rh(III)‐catalyzed direct alkenylation of arenes with readily available vinyltrifluoroborate to access functionalized styrenes. This method tolerates wide range functional groups in 33 examples excellent site‐ and regioselectivity under mild conditions. The synthetic utility was demonstrated through the further transformation thus‐obtained Preliminary mechanistic studies indicated that reaction probably proceeds an C−H activation/Suzuki coupling pathway. magnified image

Language: Английский

Transition-Metal-, Additive-, and Solvent-Free [3 + 3] Annulation of RCF2-Imidoyl Sulfoxonium Ylides with Cyclopropenones to Give Multifunctionalized CF3-Pyridones DOI

Si Wen,

Yanhui Chen,

Qingyu Tian

et al.

The Journal of Organic Chemistry, Journal Year: 2021, Volume and Issue: 87(2), P. 1124 - 1132

Published: Dec. 29, 2021

An efficient and practical strategy was developed to synthesize 1,3,4-triaryl-6-trifluoromethylpyridones from CF3-imidoyl sulfoxonium ylides cyclopropenones in good excellent yields. This stepwise [3 + 3] annulation reaction carried out under transition-metal-, additive-, solvent-free conditions, generating 1 equiv of dimethyl sulfoxide as byproduct tolerating a series functional groups.

Language: Английский

Citations

42
Recent progress in cycloaddition reactions of cyclopropenone DOI Creative Commons

Shibo Lin,

Xiang Lan, Chun Liu

et al.

Arabian Journal of Chemistry, Journal Year: 2024, Volume and Issue: 17(8), P. 105845 - 105845

Published: May 23, 2024

Cyclopropenone has emerged as a highly versatile precursor in organic synthesis due to its diverse reactivity. The cyclopropenone derivatives could undergo various transformations such cycloaddition reactions, ring-opening and isomerization reactions the presence of different chemical reagents. Over years, significant progress been made manipulation cyclopropenones for construction carbocycles, heterocycles, other useful compounds. Despite several reviews that have concerned chemistry cyclopropenones, utility motifs carbocycles heterocycles rarely reported. Herein, we report recent advancements synthetic precursors towards compounds with biological significance.

Language: Английский

Citations

3
Synthesis of Benzotriazepin-1-ones via Decarboxylative [4 + 3]-Annulation of Isatoic Anhydrides with Nitrile Imines DOI

Byung Jun Park,

Ji Yang, Sung‐Gon Kim

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(11), P. 7290 - 7301

Published: May 17, 2023

A novel and streamlined approach to synthesizing benzotriazepin-1-ones has been developed through a hexafluoroisopropanol-promoted decarboxylative cascade reaction between isatoic anhydrides hydrazonoyl chloride. The [4 + 3] annulation of hexafluoroisopropyl 2-aminobenzoates with nitrile imines, generated in situ, is key feature this innovative reaction. This offered simple efficient method for broad range structurally intricate highly functional benzotriazepinones.

Language: Английский

Citations

6
Synthesis of 2-trifluoromethylquinolines through rhodium-catalysed redox-neutral [3 + 3] annulation between anilines and CF3-ynones using traceless directing groups DOI
Haichao Huang, Hailong Wang,

Chao Gong

et al.

Organic Chemistry Frontiers, Journal Year: 2021, Volume and Issue: 9(2), P. 413 - 419

Published: Nov. 29, 2021

Rhodium-catalysed [3 + 3]-cycloaddition of acetanilides with CF 3 -ynones was achieved through a traceless directing-group strategy, which delivered 2-trifluromethylquinolines exhibiting favorable blue emissions.

Language: Английский

Citations

14
I2-DMSO Mediated Multicomponent [3+2] Annulation Reaction: An Approach to Pyrrolo[2,1-a]isoquinoline Derivatives with a Quaternary Center DOI

Shi‐Yi Zhuang,

Jinyi Liu, Hui Guo

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(46), P. 8573 - 8577

Published: Nov. 15, 2022

An I2-DMSO mediated multicomponent [3+2] cascade annulation reaction using methyl ketones, 1,2,3,4-tetrahydroisoquinolines (THIQ) and cyclopropenones as readily available substrates has been developed. This metal-free process involves N-H/α-C(sp3)-H trifunctionalization of THIQ C-C bond cleavage cyclopropenone, providing a direct approach to obtain pyrrolo[2,1-a]isoquinoline derivatives with quaternary carbon center. Two bonds one C-N are formed efficiently in pot.

Language: Английский

Citations

9
TBHP-promoted multicomponent reaction to access 2-aminobenzoxazinones using sodium chlorodifluoroacetate as the C1 synthon DOI
Huijuan Li, Yongfeng Wang, Cheng Xu

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(8), P. 1988 - 1993

Published: Jan. 1, 2023

Sodium chlorodifluoroacetate serves as the C1 synthon for constructing 2-aminobenzoxazinones via a quadruple cleavage mode under transition metal-free conditions.

Language: Английский

Citations

4
Palladium-catalysed dual ring-opening [3 + 4] annulation of isatoic anhydrides with cyclic iodoniums to build tribenzo[b,d,f]azepines and a mechanistic DFT study DOI

Lingyu Huang,

Ya-Nan Tian,

Shiyan Ren

et al.

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(22), P. 6259 - 6264

Published: Jan. 1, 2022

A palladium-catalysed dual ring-opening, decarboxylative/decarbonylative [3 + 4] annulation of isatoic anhydrides with cyclic iodoniums to build tribenzo[ b,d,f ]azepines was developed, and its mechanism studied using DFT.

Language: Английский

Citations

7
Recent Progress in the Synthesis of Benzoxazin-4-Ones, Applications in N-Directed Ortho-Functionalizations, and Biological Significance DOI Creative Commons
Ziad Moussa, Mani Ramanathan, Harbi Tomah Al‐Masri

et al.

Molecules, Journal Year: 2024, Volume and Issue: 29(23), P. 5710 - 5710

Published: Dec. 3, 2024

The development of efficient synthetic procedures to access fused N, O-heterocyclic skeletons has been a pivotal research topic in organic synthesis for several years. Owing the applications O-fused heterocycles synthesis, material sciences, and medicinal chemistry, significant efforts have dedicated design novel methods their construction. To this end, 1,3-benzoxazin-4-ones are privileged candidates molecules often found natural products, agrochemicals, materials science applications. In review, we aim summarize existing literature on from 2010 onwards. Moreover, also identified as an excellent native directing group ortho-functionalization via C-H activation, which is strenuous task requiring pre-functionalized substrates. latter part report, compiled interesting examples

Language: Английский

Citations

0
Photoinduced Regioselective Decarbonylative and Decarboxylative C–O Bond Functionalizations: Approach toward Chemoselective Scissions of Isatoic Anhydride and Unraveling the Enroutes through Control Experiments and DFT Studies DOI
Rahul Dev Mandal, Dwaipayan Das, Anindita Sarkar

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 5, 2024

Distinctive, green, innovative, and well-organized photoinduced (metal- or photocatalyst-free) regioselective decarbonylative decarboxylative C–O bond functionalization protocols to access aryl 2-aminobenzoates 2-substituted benzoxazinone derivatives in excellent yields have been devised. These are achieved through the chemoselective scission of isatoic anhydride with ketones, diaryliodonium triflate, nitroalkene, phthalazinone, phenol derivatives, which, turn, served as representative "electrophilic nucleophilic" coupling partners. Control experiments DFT calculations reveal that electrophilic radical-bearing partners specifically follow decarbonylation pathway, while nucleophilic conjugates facilitate decarboxylation process. Thus, devised methods represent fragmentation anhydride, which occurs due electronic nature Again, C–O/O–C formation is also a novel outcome this methodology. We green method for synthesizing 2-aminobenzoate-subtituted paracetamol route. A fluorescence quenching study indicates phenyl 2-aminobenzoate detects Fe(II) ions, exhibiting no reactivity toward various other metal ions. Additionally, transition-metal-catalyzed C–H vinyl sulfone was performed at ease significant yields, appreciated strategy developed by us.

Language: Английский

Citations

0
Rhodium‐Catalyzed Oxidative Coupling of Potassium Vinyltrifluoroborate with Arenes: A Direct Access to Functionalized Styrene Derivatives DOI
Wenbo Ma, Yang Wang, Bo Li

et al.

Advanced Synthesis & Catalysis, Journal Year: 2022, Volume and Issue: 364(22), P. 3881 - 3887

Published: Oct. 6, 2022

Abstract Herein, we report a Rh(III)‐catalyzed direct alkenylation of arenes with readily available vinyltrifluoroborate to access functionalized styrenes. This method tolerates wide range functional groups in 33 examples excellent site‐ and regioselectivity under mild conditions. The synthetic utility was demonstrated through the further transformation thus‐obtained Preliminary mechanistic studies indicated that reaction probably proceeds an C−H activation/Suzuki coupling pathway. magnified image

Language: Английский

Citations

1