Radical Three-Component Nitro Spiro-Cyclization of Unsaturated Sulfonamides/Amides to Access NO2-Featured 4-Azaspiro[4.5]decanes DOI

Changyou Guo,

Li‐Jun Li,

Qinqin Yan

и другие.

Organic Letters, Год журнала: 2024, Номер 26(15), С. 3069 - 3074

Опубликована: Апрель 1, 2024

Free radical three-component nitration/spirocyclization of unsaturated sulfonamides/amides with tert-butyl nitrite was developed for the construction diverse NO2-revised 4-azaspiro[4.5]decanes. This tandem system featured metal-free participation, simple operation, good selectivity/yields, and a green/low-cost O source. Meanwhile, one nitro-containing complex molecule scaled-up operation were performed well to test synthetic potential cascade reaction. Isotopic labeling, inhibition experiments, DFT analysis carried out gain insight into reaction process.

Язык: Английский

Electrooxidative palladium- and enantioselective rhodium-catalyzed [3 + 2] spiroannulations DOI Creative Commons
Wen Wei, Alexej Scheremetjew, Lutz Ackermann

и другие.

Chemical Science, Год журнала: 2022, Номер 13(9), С. 2783 - 2788

Опубликована: Янв. 1, 2022

Despite indisputable progress in the development of electrochemical transformations, electrocatalytic annulations for synthesis biologically relevant three-dimensional spirocyclic compounds has as yet not been accomplished. In sharp contrast, herein, we describe palladaelectro-catalyzed C-H activation/[3 + 2] spiroannulation alkynes by 1-aryl-2-naphthols. Likewise, a cationic rhodium(iii) catalyst was shown to enable electrooxidative [3 spiroannulations via formal C(sp3)-H activations. The versatile featured broad substrate scope, employing electricity green oxidant lieu stoichiometric chemical oxidants under mild conditions. An array enones and diverse spiropyrazolones, bearing all-carbon quaternary stereogenic centers were thereby accessed user-friendly undivided cell setup, with molecular hydrogen sole byproduct.

Язык: Английский

Процитировано

72

Electrochemical electrophilic bromination/spirocyclization of N-benzyl-acrylamides to brominated 2-azaspiro[4.5]decanes DOI
Zhongyi Zhang,

Zhong‐Wei Hou,

Hao Chen

и другие.

Green Chemistry, Год журнала: 2023, Номер 25(9), С. 3543 - 3548

Опубликована: Янв. 1, 2023

An electrochemical electrophilic bromination/spirocyclization of N -benzyl-acrylamides to brominated 2-azaspiro[4.5]decanes with 2-bromoethan-1-ol as the brominating reagent has been developed.

Язык: Английский

Процитировано

51

Electrochemical Trifluoromethylthiolation and Spirocyclization of Alkynes with AgSCF3: Access to SCF3-Containing Spiro[5,5]trienones DOI
Wenchao Yang, Mingming Zhang, Yu Sun

и другие.

Organic Letters, Год журнала: 2021, Номер 23(17), С. 6691 - 6696

Опубликована: Авг. 16, 2021

A novel and efficient strategy for trifluoromethylthiolation dearomatization of activated alkynes with stable readily available AgSCF3 has been developed. Reported herein is the unprecedented electrochemical generation SCF3 radical in absence persulfate synthesis SCF3-containing spiro[5,5]trienones good yields via a 6-exo-trig cyclization.

Язык: Английский

Процитировано

79

Electrochemical Dearomative Spirocyclization DOI
Nan Li, Zhaojiang Shi,

Wei‐Zhen Wang

и другие.

Chemistry - An Asian Journal, Год журнала: 2023, Номер 18(9)

Опубликована: Март 15, 2023

Electrochemical dearomative spirocyclization serves as a green and sustainable approach to convert the flat, two-dimension aromatic feedstock into value-added three-dimension spirocyclic architectures. This review highlights recent advances, emphasizes mechanistic discussions, showcases synthetic applications of this emerging versatile powerful transformation.

Язык: Английский

Процитировано

36

Electrochemical Selenylative Carbannulation of Biaryl Ynones to Seleno-Dibenzocycloheptenones/Spiro[5.5]Trienones DOI
Chada Raji Reddy, Dattahari H. Kolgave

The Journal of Organic Chemistry, Год журнала: 2021, Номер 86(23), С. 17071 - 17081

Опубликована: Ноя. 22, 2021

Electrooxidative-induced synthesis of structurally diverse seleno-dibenzocyclohepten-5-ones and seleno-spiro[5.5]trienones by selenylative carbannulation biaryl ynones with diaryl diselenide has been developed. The switchable reactivity, intramolecular ortho-annulation or dearomative ipso-annulation, is directed the substituent present on ortho-aryl group aryl-ynone. prominent features this method include metal-free, external chemical oxidant-free conditions, readily accessible substrates.

Язык: Английский

Процитировано

55

Selective Fluoromethyl Couplings of Alkynes via Nickel Catalysis DOI
Huan Li, Fang Wang, Shengqing Zhu

и другие.

Angewandte Chemie International Edition, Год журнала: 2021, Номер 61(9)

Опубликована: Дек. 28, 2021

We describe here a Ni-catalyzed intermolecular carbo-fluoromethylation of alkynes with aliphatic halides and fluoromethyl (BrCF2 H ICH2 F) in the presence zinc, enabling facile selective access to diverse range biologically valuable CF2 H/CH2 F-incorporated alkenes excellent regio- stereoselectivity. Notably, merging intramolecular radical cyclization coupling enables expedient constructions lactones lactams high efficiency selectivity. Mechanistic studies disclose that this catalytic protocol proceeds via addition an alkyne followed by unit.

Язык: Английский

Процитировано

42

Visible-light-induced novel cyclization of 2-(2-(arylethynyl)benzylidene)-malononitrile derivatives with 2,6-di(tert-butyl)-4-methylphenol to bridged spirocyclic compounds DOI
Xiaofei Xie, Lei Wang, Quan Zhou

и другие.

Chinese Chemical Letters, Год журнала: 2022, Номер 33(12), С. 5069 - 5073

Опубликована: Март 23, 2022

Язык: Английский

Процитировано

38

Electrochemical Dearomatizing Spirocyclization of Alkynes with Dimethyl 2-Benzylmalonates to Spiro[4.5]deca-trienones DOI
Laiqiang Li,

Zhong‐Wei Hou,

Pinhua Li

и другие.

The Journal of Organic Chemistry, Год журнала: 2022, Номер 87(13), С. 8697 - 8708

Опубликована: Июнь 9, 2022

An electrochemical dearomatizing spirocyclization of alkynes with dimethyl 2-benzylmalonates for the preparation spiro[4.5]deca-trienones has been developed. This approach adopts ferrocene (Cp2Fe) as an electrocatalyst to produce carbon-centered radical intermediates from C–H-based malonates, which obviates forthputting noble-metal reagents, sacrificial chemical oxidants and 2-bromomalonates. A wide variety spiro compounds are efficiently prepared satisfactory results under mild conditions.

Язык: Английский

Процитировано

33

Iron‐Catalyzed Silylation and Spirocyclization of Biaryl‐Ynones: A Radical Cascade Process toward Silylated Spiro[5.5]trienones DOI
Fei Chen, Zheng Yang, Hao Yang

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2022, Номер 364(9), С. 1537 - 1542

Опубликована: Март 11, 2022

Abstract Iron‐catalyzed cascade silyl radical addition/6‐ exo ‐trig cyclization/dearomatization of biaryl ynones has been developed. This approach uses silane as the precursor well silylation reagent, 1,10‐phenanthroline ligand, and tert ‐butyl hydroperoxide (TBHP) oxidant. By employing this tandem process, a series silylated spiro[5.5]trienones were prepared. magnified image

Язык: Английский

Процитировано

32

Synthesis of polychloromethylated and halogenated spiro[5,5]trienones via dearomative spirocyclization of biaryl ynones DOI
Junnan Li,

Zi-Jie Li,

Liu‐Yu Shen

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2022, Номер 20(33), С. 6659 - 6666

Опубликована: Янв. 1, 2022

A selective polychloromethylation and halogenation reaction of alkynes via a radical addition/spirocyclization cascade sequence was developed, in which applying polyhaloalkanes as the precursor polyhalomethyl halogen radicals.

Язык: Английский

Процитировано

32