A Computational Study on the Radical Cascade Cyclization Mechanism of Synthesis of Benzo[b]oxepinones and Chromanes DOI
Meryem Fıstıkçı

ChemistrySelect, Год журнала: 2023, Номер 8(18)

Опубликована: Май 10, 2023

Abstract A computational study on the reaction mechanism of effective synthesis sulfonated benzo[ b ]oxepinones and chromanes by radical cascade cyclization is carried out employing density functional theory (DFT). Based our computations, rate‐determining step formation arylsulfonyl for scheme. Our calculations show that 1,8‐ 1,7‐enynes with proceeds forming more thermodynamically stable intermediates. Therefore, 1,8‐enynes prefer 7‐ exo ‐trig cyclization, while 6‐ cyclization. computations are consistent experimental results 1,7‐enynes. Moreover, if in a proton‐free solvent, elimination product can be obtained from 1,7‐enyne.

Язык: Английский

Photoinduced sulfonylation cyclization to medium-sized benzo[b]azocine and mechanistic insight DOI
Dongyang Zhao, Kai Sun, Miao Tian

и другие.

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(13), С. 3313 - 3320

Опубликована: Янв. 1, 2023

A novel light induced 8-endo sulfonyl cyclization to medium-sized benzo[ b ]azocines is developed. DFT calculations rationalize the rate-determining step and chemoselectivity observed in this transformation.

Язык: Английский

Процитировано

5

NHC-Catalyzed Tandem Reaction: A Strategy for the Synthesis of 2-Pyrrolidinone-Functionalized Phenanthridines DOI
Nengneng Zhou, Lei Wang,

Fangli Zhao

и другие.

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(23), С. 16556 - 16565

Опубликована: Ноя. 16, 2023

Herein, an N-heterocyclic carbene (NHC)-catalyzed tandem cyclization/addition/cyclization reaction of 2-isocyanobiaryls and α-bromo-N-cinnamylamides for the synthesis 2-pyrrolidinone-functionalized phenanthridines is developed. This protocol features a radical cascade process, broad substrate scope, good functional group compatibility under metal- oxidant-free conditions.

Язык: Английский

Процитировано

5

Radical Difunctionalization of Unsaturated Hydrocarbons Employing the Same Functional Reagent DOI

Wen‐Chan Tian,

Nan‐Nan Dai,

Yunpeng Lu

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(17), С. 3524 - 3541

Опубликована: Июль 3, 2024

Abstract The radical difunctionalization of unsaturated hydrocarbons serves as an efficient means to rapidly construct molecular skeletons and synthesize‐highly valuable compounds. In this transformational process, diverse positions within are sequentially functionalized by a single precursor reagent, thereby achieving highly selective transformations that promote atom economy. Furthermore, approach minimizes the generation numerous byproducts stemming from cross‐coupling reactions between reactants, owing reduction number participating components. Therefore, review provides in‐depth analysis utilizing functional reagent in recent decades. discussion is based on eight different classes (carbon‐, nitrogen‐, phosphine‐, oxygen‐, sulfur‐, selenium‐, tellurium‐, chlorine‐centered radicals), emphasizing mechanism specific difunctionalization. It also analyzes detail regulation key factors such regional selectivity, unique insights into reaction transformations.

Язык: Английский

Процитировано

1

Visible Light‐Induced Copper‐Catalyzed Alkylation/exo‐Cyclization of 1,7‐Dienes with Sulfonium Salts to Access Sulfur‐Containing Polycyclic Compounds DOI

Xin‐Qian Liu,

Jian‐Hong Fan, Kewen Tang

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер unknown

Опубликована: Июль 9, 2024

Abstract A direct visible‐light‐promoted radical‐triggered tandem cyclization of 1,7‐diene systems with cyclic sulfonium salts by using copper(I)‐based complexes as photoredox catalyst is developed. With this approach, a variety sulfur‐containing polycyclic derivatives are prepared through alkylation/ 6‐exo‐trig cyclization/ 5‐exo‐trig under mild conditions. In addition, the photoinduced copper‐catalyzed ring‐opening provides alkyl radical intermediates, which prefers addition to C−C double bond that connected aromatic ring rather than electron‐deficient vinyl in 1,7‐dienes. Moreover, oxidation desired products strategy for preparation remote nitrogen‐fused substituted sulfoxide or sulfone‐containing derivatives.

Язык: Английский

Процитировано

1

Dual Photoredox/Nickel-Catalyzed Dehydrative Difluoroalkylation of Benzyl Alcohols for the Synthesis of Allylic gem-Difluorides DOI

Yu-Yang Bai,

Liping Cao, Siyuan Li

и другие.

Organic Letters, Год журнала: 2023, Номер 25(35), С. 6511 - 6516

Опубликована: Авг. 28, 2023

A photoredox/Lewis acid cooperative catalytic system has been developed for the construction of Cvinyl–CRf bonds through dehydrative difluoroalkylation benzyl alcohols. variety allylic gem-difluorides could be obtained in moderate yields with good to excellent E/Z selectivity. In addition, several control experiments have explored, and a possible mechanism was proposed this process.

Язык: Английский

Процитировано

2

Visible‐Light‐Promoted Fluoroalkylative Cyclization of N‐Allyl‐4,5‐dihydro‐3H‐1‐benzazepin‐2‐amines: Effective Synthesis of Fluoroalkylated Imidazobenzazepines DOI
Ivanna Yu. Danyliuk, Валентина ТОЛМАЧОВА, Svitlana V. Shishkina

и другие.

ChemistrySelect, Год журнала: 2023, Номер 8(13)

Опубликована: Апрель 4, 2023

Abstract A new preparatively convenient approach to the synthesis of biopromising 1‐fluoroalkyl‐substituted 2,4,5,6‐tetrahydro‐1 H ‐imidazo[1,2‐ a ][1]benzazepines has been developed, based on chemoselective photoreduction‐catalyzed fluoroalkylation cyclization N ‐allyl‐4,5‐dihydro‐3 ‐1‐benzazepin‐2‐amines in presence fluorescein as an organocatalyst. The use comparatively inexpensive perfluoroalkyl iodides (R f I), mild reaction conditions and wide range substituents introduced make this method very attractive for preparation imidazobenzazepines with variety fluorinated moieties.

Язык: Английский

Процитировано

1

A Practical Synthesis of 2‐Arylimino‐2H‐Chromenes via Biocatalytic System in Water DOI
Jinglin Ma, Fengxi Li,

Yuelin Xu

и другие.

ChemistrySelect, Год журнала: 2023, Номер 8(20)

Опубликована: Май 24, 2023

Abstract A metal‐free, straightforward, non‐hazardous reagent‐added, one‐pot approach for the efficient synthesis of 2‐arylimino‐2 H ‐chromenes with high yields was developed first time in this report through coupling salicylaldehydes β‐ketothioamides, which catalyzed by lipase water. This green strategy provides an method to obtain various and enriches practical application biocatalysis.

Язык: Английский

Процитировано

1

Synthesis of Acylation Polycyclic Derivatives via Regioselective Acylation/Cyclization of 1,7-Dienes with Acyl Oxime Esters DOI

Shun‐Dan Li,

Biquan Xiong, Kewen Tang

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(16), С. 11233 - 11243

Опубликована: Июль 25, 2024

A visible-light-induced radical cascade regioselective acylation/cyclization of 1,7-dienes with acyl oxime esters for the preparation acylation polycyclic compounds via NCR-mediated C-C σ-bond cleavage is established. The transformation involves in and selective addition electron neutral C═C bonds synthesis quinolinone derivatives, not traditional seven-membered ring products. strategy offers several advantages, including broad substrate tolerance, no need bases, hyperstoichiometric initiators, other auxiliaries.

Язык: Английский

Процитировано

0

Oxy-difluoroallylation of Ynamides by Nickel-Catalyzed Tandem Alkoxylation/Claisen Rearrangement DOI

Haotian Gao,

Tiebo Xiao,

Yubo Jiang

и другие.

Organic Letters, Год журнала: 2024, Номер 26(41), С. 8832 - 8836

Опубликована: Окт. 9, 2024

A nickel-catalyzed tandem alkoxylation/claisen rearrangement strategy for the oxy-difluoroallylation of ynamides has been developed. In this reaction, 3,3-difluoroallyl alcohol was used as a fluorine-containing building block to construct C–CF2 bond first time. This approach is recognized its robust tolerance functional groups, impressive yields, and excellent atomic efficiency, all achieved under mild reaction conditions. series β,β-difluoromethyleneamide derivatives were efficiently obtained through simple operations, their practicality confirmed gram-scale synthesis product derivatization.

Язык: Английский

Процитировано

0

Rh(iii)-catalyzed (5 + 2)-cycloaddition reactions of ortho-hydroxyethyl phenols with internal alkynes: efficient synthesis of benzoxepines DOI

Pratiksha Bhorali,

Jyotshna Phukon,

Sanjib Gogoi

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2023, Номер 21(12), С. 2516 - 2523

Опубликована: Янв. 1, 2023

An unprecedented (5 + 2)-cycloaddition reaction of ortho-hydroxyethyl phenol and internal alkyne was developed. This Rh(III)-catalyzed provided benzoxepine derivatives which have very high biological significance. A wide range phenols alkynes were studied to provide the benzoxepines in yields.

Язык: Английский

Процитировано

0