Rh(III)‐Catalyzed Diverse C—H Functionalization of Iminopyridinium Ylides DOI
Zhenzhen Dong, Pengfei Li, Xingwei Li

и другие.

Chinese Journal of Chemistry, Год журнала: 2021, Номер 39(9), С. 2489 - 2494

Опубликована: Май 9, 2021

Main observation and conclusion Divergent synthesis of useful skeletons has been realized via rhodium(III)‐catalyzed C—H activation iminopyridinium ylides coupling with various unsaturated reagents. Isocoumarins isoquinolones were obtained cleavage the C—N or N—N bond in ylidic directing group, while fluorinated alkenes delivered group intact. The reactions occurred wide substrate scopes good efficiency under redox‐neutral air‐tolerant conditions. Representative products exhibit solid‐state fluorescent property bioactivity inhibition toward human cancer cells.

Язык: Английский

Recent advances in the Rh-catalyzed cascade arene C–H bond activation/annulation toward diverse heterocyclic compounds DOI
Chang Wang, Fan Chen, Peng‐Cheng Qian

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2021, Номер 19(8), С. 1705 - 1721

Опубликована: Янв. 1, 2021

A review highlighting the advances in Cp*Rh(iii) catalysed cascade arene C–H activation/annulation including application, scope, limitations and mechanism of these transformations.

Язык: Английский

Процитировано

49

Rhodium(III)-Catalyzed Atroposelective Synthesis of C–N Axially Chiral Naphthylamines and Variants via C–H Activation DOI
Peiyuan Wang, Yaling Huang,

Jierui Jing

и другие.

Organic Letters, Год журнала: 2022, Номер 24(13), С. 2531 - 2535

Опубликована: Март 30, 2022

Reported herein is the efficient and atroposelective construction of two categories C-N atropisomers via rhodium(III)-catalyzed C-H activation sulfoxonium ylides en route to [4+2] annulation with sterically hindered, electron-rich alkynes. This reaction proceeds high regio- enantioselectivity under redox-neutral conditions a double-substrate strategy, providing novel entry axially chiral 4-functionalized 1-naphthols.

Язык: Английский

Процитировано

39

Metal-Free Syntheses of α-Ketothioamide and α-Ketoamide Derivatives from Sulfoxonium Ylides DOI

Trayambek Nath Chaubey,

Paran J. Borpatra, Ajay Sharma

и другие.

Organic Letters, Год журнала: 2022, Номер 24(43), С. 8062 - 8066

Опубликована: Окт. 24, 2022

An efficient base, additive and metal-free synthetic methods for α-ketothioamide α-ketoamide derivatives from readily available sulfoxonium ylides have been described. Sulfoxonium with primary or secondary amines afforded α-ketothioamides in the presence of elemental sulfur, whereas α-ketoamides were produced when I2 TBHP present. The reaction proceeded well at room temperature generated corresponding molecules good to excellent yields. can be scaled-up tolerated by a range functional groups simple operational procedures.

Язык: Английский

Процитировано

37

Photo-Thermo-Mechanochemical Approach to Synthesize Quinolines via Addition/Cyclization of Sulfoxonium Ylides with 2-Vinylanilines Catalyzed by Iron(II) Phthalocyanine DOI
Luyao Liu,

Jingyang Lin,

Mingxuan Pang

и другие.

Organic Letters, Год журнала: 2022, Номер 24(5), С. 1146 - 1151

Опубликована: Фев. 3, 2022

A novel photo-thermo-mechanochemical approach to assembling quinolines catalyzed by iron(II) phthalocyanine has been realized for the first time. This transformation features a cost-efficient catalytic system and operational simplicity, is free of solvent, shows good substrate tolerance, providing green alternative existing thermal approaches. Mechanistic experiments demonstrate that in-situ-formed secondary amine may be key intermediate further cyclization/aromatization process.

Язык: Английский

Процитировано

30

Divergent Synthesis of Tetrasubstituted Phenols via [3 + 3] Cycloaddition Reaction of Vinyl Sulfoxonnium Ylides with Cyclopropenones DOI
Shaoyong Chen, Yao‐Fu Zeng,

Wen‐Xuan Zou

и другие.

Organic Letters, Год журнала: 2023, Номер 25(23), С. 4286 - 4291

Опубликована: Июнь 2, 2023

Two categories of tetrasubstituted phenols were prepared via the cycloaddition reaction vinyl sulfoxonnium ylides with cyclopropenones in a switchable manner. Copper carbenoid was proposed as active intermediate process 2,3,4,5-tetrasubstituted formation, while 2,3,5,6-tetrasubstituted generated direct [3 + 3] annulation under metal-free conditions. Further synthetic applications also demonstrated.

Язык: Английский

Процитировано

22

Metal-free cascade O–H double insertion between I(III)/S(VI)-ylides, carboxylic acids, and alcohols: modular access to unsymmetrical α,α-O,O-substituted ketones DOI

Jiaohang Wei,

Wen‐Xuan Zou,

Qiong Hu

и другие.

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(11), С. 3234 - 3241

Опубликована: Янв. 1, 2024

Herein, we present a cascade O–H double insertion reaction between I (III) /S (VI) -ylides, carboxylic acids, and alcohols under metal-free conditions, enabling the modular synthesis of unsymmetrical α,α- O , -substituted ketones.

Язык: Английский

Процитировано

8

A Platform for the Synthesis of Diverse Phosphonyl and Thiofunctionalized Sulfoxonium Ylides DOI

Wen‐Xuan Zou,

Qiong Hu,

Dan‐Ting Shen

и другие.

Organic Letters, Год журнала: 2024, Номер 26(27), С. 5811 - 5816

Опубликована: Июнь 28, 2024

A practical strategy for the construction of diverse phosphonyl and thiofunctionalized sulfoxonium ylides via controllable monofunctionalization hybrid I(III)/S(VI) is presented. This process allows efficient P–H insertion under Cu catalysis, enabling synthesis ylides, whereas reaction with sulfur-containing reagents including AgSCF3, KSC(S)OR, KSCN mild conditions resulted in α-trifluoromethylthiolation, dithiocarbanation, thiocyanation accordingly. Of note, wide substrate compatibility (108 examples), excellent efficiency (up to 99% yield), gram-scale experiments, various product derivatizations highlight synthetic utility this protocol.

Язык: Английский

Процитировано

7

Sulfoxonium-Ylide-Directed C–H Activation and Tandem (4 + 1) Annulation DOI
Vinayak Hanchate, Ravi Devarajappa, Kandikere Ramaiah Prabhu

и другие.

Organic Letters, Год журнала: 2020, Номер 22(8), С. 2878 - 2882

Опубликована: Март 31, 2020

Rh(III)-catalyzed C-H activation and cyclization of sulfoxonium ylide with acrylates leads to an efficient synthesis indanone derivatives. The reaction proceeds under mild external metal-oxidant-free conditions. acts as a traceless directing group well internal oxidant. (4 + 1) Annulation after the formation carbocyclic ring, byproduct obtained is DMSO, which can be easily separated.

Язык: Английский

Процитировано

50

Recent advances in the synthesis of bridgehead (or ring-junction) nitrogen heterocycles via transition metal-catalyzed C–H bond activation and functionalization DOI Open Access

Biao Nie,

Wanqing Wu, Ying‐Jun Zhang

и другие.

Organic Chemistry Frontiers, Год журнала: 2020, Номер 7(19), С. 3067 - 3099

Опубликована: Янв. 1, 2020

An update on recent advances in the synthesis of bridgehead nitrogen fused heterocycles via transition metal-catalyzed C–H activation and functionalization is reported.

Язык: Английский

Процитировано

44

A Cascade Rh(III)‐catalyzed C−H Activation/Chemodivergent Annulation of N‐carbamoylindoles with Sulfoxonium Ylides for the Synthesis of Dihydropyrimidoindolone and Tricyclic [1,3]Oxazino[3,4‐a]indol‐1‐ones Derivatives DOI
Hui Xie,

Mei Zhong,

Hua‐Jie Kang

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2021, Номер 363(5), С. 1436 - 1442

Опубликована: Янв. 21, 2021

Abstract A highly efficient cascade Rh(III)‐catalyzed C−H activation/intramolecular chemodivergent cyclization reaction of N‐carbamoylindoles and sulfoxonium ylides has been successfully achieved for the first time. This synergistic process provides rapid access to functionalized dihydropyrimidoindolone tricyclic [1,3]oxazino[3,4‐ a ]indol‐1‐ones skeletons under redox neutral conditions with broad substrate scope remarkable functional‐group compatibility. Further late‐stage modification structurally complex drug molecules mechanistic studies were also accomplished. magnified image

Язык: Английский

Процитировано

40