Light‐Induced Domino and Multicomponent Reactions: How to Reach Molecular Complexity without a Catalyst DOI Creative Commons
Polyssena Renzi, Jacopo Scarfiello, Alberto Lanfranco

и другие.

European Journal of Organic Chemistry, Год журнала: 2023, Номер unknown

Опубликована: Авг. 31, 2023

Abstract Achieving high molecular complexity can be not trivial, but the exploitation of domino reactions provides an atom‐ and step‐economical method to reach this target. Over past decades, a lot efforts have been put on development photocatalytic cascades employing both metal‐based purely organic catalysts. Despite effectiveness these protocols, catalyst‐ additive‐free light‐induced are gaining momentum thank their efficiency, operational simplicity sustainability. The increasing number papers published field in last years is proof appeal transformations. In Review, we discuss multicomponent mediated by light with focus photocatalyst‐ processes. most recent advances synthesis complex nitrogen‐, oxygen‐, sulphur‐ selenium‐heterocycles together analysed emphasis experimental mechanistic studies.

Язык: Английский

Acyl Radicals from α-Keto Acids: Metal-Free Visible-Light-Promoted Acylation of Heterocycles DOI
Hu-Lin Zhu,

Fan‐Lin Zeng,

Xiaolan Chen

и другие.

Organic Letters, Год журнала: 2021, Номер 23(8), С. 2976 - 2980

Опубликована: Март 29, 2021

A general and metal-free visible-light-induced decarboxylative arylation procedure at room temperature was described for the construction of acylated heterocyclic derivatives, such as benzimidazo/indolo[2,1-a]isoquinolin-6(5H)-ones, aroylazaspiro[4.5]trienones, thioflavones, so on. This practical conducted by using 2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile (4CzIPN) a photocatalyst under mild conditions, which avoided use an additional base, traditional heating, metal reagents.

Язык: Английский

Процитировано

125

Organoelectrophotocatalytic Generation of Acyl Radicals from Formamides and Aldehydes: Access to Acylated 3-CF3-2-Oxindoles DOI
Hong He,

Qinhui Wan,

Zhong‐Wei Hou

и другие.

Organic Letters, Год журнала: 2023, Номер 25(38), С. 7014 - 7019

Опубликована: Сен. 18, 2023

Organoelectrophotocatalytic generation of acyl radicals from formamides and aldehydes to synthesize acylated 3-CF3-2-oxindoles has been developed. This protocol features a monocatalytic system using 9,10-phenanthrenequinone (PQ) both as catalyst hydrogen atom transfer (HAT) reagent, which avoids the use an external HAT metal oxidant. A variety have obtained in satisfactory yields CF3-substituted N-arylacrylamides via tandem radical cyclization.

Язык: Английский

Процитировано

49

Electrochemical Oxidative Halogenation of N-Aryl Alkynamides for the Synthesis of Spiro[4.5]trienones DOI

Ke Yu,

Xianqiang Kong,

Jiajun Yang

и другие.

The Journal of Organic Chemistry, Год журнала: 2020, Номер 86(1), С. 917 - 928

Опубликована: Дек. 7, 2020

We developed a green method for the synthesis of spiro[4.5]trienones through an electrochemical oxidative halocyclization with N-aryl alkynamides. This reaction was conducted under metal-catalyst- and exogenous-oxidant-free conditions at room temperature. Using readily available LiCl, LiBr, LiI as halogen source, variety dearomative halo-spirocyclization products were obtained in good to excellent yields broad scope functional group tolerance.

Язык: Английский

Процитировано

62

Visible-light-induced metal-free cascade cyclization of N-arylpropiolamides to 3-phosphorylated, trifluoromethylated and thiocyanated azaspiro[4.5]trienones DOI

Fan‐Lin Zeng,

Xiaolan Chen, Kai Sun

и другие.

Organic Chemistry Frontiers, Год журнала: 2020, Номер 8(4), С. 760 - 766

Опубликована: Дек. 21, 2020

Photocatalytic strategies for the preparation of 3-functionalized azaspiro[4.5]trienones via a radical-initiated cascade annulation reaction was developed.

Язык: Английский

Процитировано

57

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

A Domino Dearomative ipso-Annulation/Desymmetrization Approach: Stereoselective Access to Tricyclic Alkaloid Skeletons DOI
Chada Raji Reddy,

A. Prasad,

Uprety Ajaykumar

и другие.

Organic Letters, Год журнала: 2024, Номер 26(23), С. 4904 - 4909

Опубликована: Июнь 5, 2024

Herein, we reveal an unprecedented domino annulation of

Язык: Английский

Процитировано

9

Metal-free spirocyclization of N-arylpropiolamides with glyoxylic acids: access to complex azaspiro-fused tricycles DOI
Akshay M. Nair, Anand H. Shinde, Shreemoyee Kumar

и другие.

Chemical Communications, Год журнала: 2020, Номер 56(82), С. 12367 - 12370

Опубликована: Янв. 1, 2020

An efficient K2S2O8-mediated oxidative cascade spirocyclization of N-arylpropiolamides with aryl glyoxylic acids was demonstrated for constructing azaspiro[4,5]-trienones and complex azaspiro-fused architectures.

Язык: Английский

Процитировано

45

Visible-Light-Mediated Hydroacylation of Azobenzenes with α-Keto Acids DOI
Jingya Yang,

Menghui Song,

Hongyan Zhou

и другие.

Organic Letters, Год журнала: 2020, Номер 22(21), С. 8407 - 8412

Опубликована: Окт. 13, 2020

A visible-light-mediated protocol for the hydroacylation of azobenzenes with α-keto acids has been developed. In absence any catalyst or additive, decarboxylative proceeded smoothly under visible-light irradiation at room temperature. wide range and were well-tolerated afforded products in high to excellent yields. Preliminary investigations indicated that photoactive absorb visible light enable transformation.

Язык: Английский

Процитировано

43

Eosin Y as a direct hydrogen-atom transfer photocatalyst for the C3-H acylation of quinoxalin-2(1H)-ones DOI
Hangcheng Ni, Yu Li,

Xingzi Shi

и другие.

Tetrahedron Letters, Год журнала: 2021, Номер 68, С. 152915 - 152915

Опубликована: Фев. 15, 2021

Язык: Английский

Процитировано

37

Visible‐Light‐Mediated Nitrogen‐Centered Radical Strategy: Preparation of 3‐Acylated Spiro[4,5]trienones DOI
Pu Chen, Jun Xie, Zan Chen

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2021, Номер 363(18), С. 4440 - 4446

Опубликована: Июль 23, 2021

Abstract A nitrogen‐centered radical strategy for the preparation of 3‐acylated spiro[4,5]trienones via visible‐light‐mediated acylation/ ipso ‐cyclization alkynes with acyl oxime esters is reported. The alkyl‐ and aryl‐substituted radicals, which generate from cleavage carbon‐carbon σ ‐bonds in pathway, attack triple bonds propiolamides then undergo ‐cyclization. This method provides a way construction 3‐acyl‐substituted spiro[4,5]trienones, can introduce aryl‐ or alkyl‐substituted into spiro[4,5]trienone skeletons. magnified image

Язык: Английский

Процитировано

34