Desenvolvimento de metodologias fotoquímicas na região do visível envolvendo arildiazoacetatos DOI Open Access

Marcelo Duarte da Costa

Опубликована: Авг. 26, 2022

The endeavor for the development of new synthetic methods aims at creation routes and/ or manufacture molecules.Photochemical reactions can open opportunities considering both these aspects.In particular, use visible region electromagnetic spectrum has been recently intensively explored by organic synthesis community; and represents a powerful strategy technologies.In this context, our research group is also interested in area focusing recent years on chemistry diazo compounds.In Master Dissertation, two projects were developed based photochemistry aryldiazoacetates, which produce free carbenes from blue light irradiation (450 -470 nm).The first project involved C-C insertion 1,3diketones onto aryldiazoacetates to afford corresponding 1,4-dicarbonyl compounds.This class products fully substituted carbon center, be accessed even presence bulky groups.10 examples synthesized with yields varying between 51 73%, characterized IR, HRMS NMR techniques.X-ray analyzes performed when necessary unequivocally prove chemical structure class.In study, it was possible determine trend bond breaking event non-symmetrical 1,3diketone, depending substituents present reaction mechanism proposed collected experimental evidence.The second mixture oximes different solvents, DCM THF (or other cyclic ethers).In DCM, one observes direct O-H oxime aryldiazoacetate.In ethers), notes more complex involving ring-opening ether incorporation compound their ends, thus unveiling multicomponent reaction.The molecules prepared following are unprecedented possibly display potential biological activity.12 insertions associated ethers produced 46 95%.These compounds using EMAR techniques.

Язык: Английский

Visible Light-Induced Reactions of Diazo Compounds and Their Precursors DOI
Ziyan Zhang, Vladimir Gevorgyan

Chemical Reviews, Год журнала: 2024, Номер 124(11), С. 7214 - 7261

Опубликована: Май 16, 2024

In recent years, visible light-induced reactions of diazo compounds have attracted increasing attention in organic synthesis, leading to improvement existing reactions, as well the discovery unprecedented transformations. Thus, photochemical or photocatalytic generation both carbenes and radicals provide milder tools toward these key intermediates for many valuable However, vast majority transformations represent new reactivity modes compounds, which are achieved by decomposition photoredox catalysis. particular, use a redox-active photocatalysts opens avenue plethora radical reactions. The application methods led inaccessible classical associated with metal carbenes. most cases, act sources but can also serve acceptors. Importantly, described processes operate under mild, practical conditions. This Review describes this subfield compound chemistry, particularly focusing on advancements.

Язык: Английский

Процитировано

60
Visible light-mediated photolysis of organic molecules: the case study of diazo compounds DOI
Rafael D. C. Gallo, Guilherme Cariello Silva, Tales A. C. Goulart

и другие.

Chemical Communications, Год журнала: 2023, Номер 59(48), С. 7346 - 7360

Опубликована: Янв. 1, 2023

This article discusses the photochemistry of several diazo compounds undergoing visible light-mediated photolysis to generate free carbenes (or other highly reactive intermediates), which can be sequentially trapped by different reacting partners.

Язык: Английский

Процитировано

46
Visible-Light-Mediated Formal Carbene Insertion Reaction: Enantioselective Synthesis of 1,4-Dicarbonyl Compounds Containing All-Carbon Quaternary Stereocenter DOI
Hua Zhang,

Zheyuan Wang,

Zirui Wang

и другие.

ACS Catalysis, Год журнала: 2022, Номер 12(9), С. 5510 - 5516

Опубликована: Апрель 25, 2022

We developed an efficient visible-light-mediated formal carbene insertion reaction of 1,3-diketones with diazoesters for the construction enantioenriched 1,4-dicarbonyl compounds a quaternary carbon center. Combining visible light and Brønsted acid catalyst, chiral were achieved in good yields high enantioselectivities by photochemical transfer protocol.

Язык: Английский

Процитировано

43
Visible photons as ideal reagents for the activation of coloured organic compounds DOI Creative Commons
Lorenzo Di Terlizzi, Luca Nicchio,

Stefano Protti

и другие.

Chemical Society Reviews, Год журнала: 2024, Номер 53(10), С. 4926 - 4975

Опубликована: Янв. 1, 2024

In search for the perfect wave(length). This review is dedicated to recent efforts in development of visible light driven photochemical strategies occurring coloured organic compounds.

Язык: Английский

Процитировано

12
A visible light-mediated three-component strategy based on the ring-opening of cyclic ethers with aryldiazoacetates and nucleophiles DOI
Mateus L. Stivanin, Rafael D. C. Gallo, João Paulo M. Spadeto

и другие.

Organic Chemistry Frontiers, Год журнала: 2022, Номер 9(5), С. 1321 - 1326

Опубликована: Янв. 1, 2022

A visible light-mediated strategy insensitive to air or moisture allows a 3-component reaction between aryldiazoacetates, cyclic ethers and various nucleophiles afford formal O–H inserted products of more complex alcohols.

Язык: Английский

Процитировано

28
Visible-Light-Induced Imide Synthesis through a Nitrile Ylide Formation/Trapping Cascade DOI
Bao‐Gui Cai,

Wei‐Zhong Yao,

Lei Li

и другие.

Organic Letters, Год журнала: 2022, Номер 24(36), С. 6647 - 6652

Опубликована: Сен. 2, 2022

A visible-light-promoted three component reaction of diazo compounds, nitriles, and carboxylic acids is reported. The utilizes acceptor-only compounds as carbene precursors nitriles carbene-trapping reagents to form the key nitrile ylides. Under optimal conditions, a wide range imide products were obtained in good excellent yields. gram-scale synthesis synthetic application isoquinoline-1,3(2H,4H)-dione derivatives further proved value this method.

Язык: Английский

Процитировано

20
Catalyst-free electro-photochemical insertion reactions of carbene anion radicals by convergent paired electrolysis DOI Creative Commons

Shweta Singh,

Suchismita Rath,

Subhankar Bera

и другие.

Cell Reports Physical Science, Год журнала: 2024, Номер 5(5), С. 101944 - 101944

Опубликована: Май 1, 2024

Paired electrolysis is an energy-efficient electrochemical reaction where both anodic and cathodic electron flow directly induces product formation with maximum faradaic efficiency. Herein we report a metal-free convergent pair electro-photochemical strategy to generate radical cation anion that resulted in the N-alkylation of various N-heterocycles, amines, sulfonamides. The also facilitated site-selective CH-alkylation benzo fused morpholine, indolines, OH- SH- alkylation phenols thiophenols aryl diazo esters. Mild condition such as 5 mA constant current W blue LED were sufficient complete within 2 h. Late-stage APIs sulfadiazines privileged scaffolds like sulfonamides diazepanes have been achieved successfully. This paired photo-electrolysis establishes new way achieve important reactions better productivity shorter time over existing strategies.

Язык: Английский

Процитировано

4
Visible-Light-Initiated Multicomponent Reactions of α-Diazoesters to Access Organophosphorus Compounds DOI

Chengming Qu,

Jindong Hao,

Hongyu Ding

и другие.

The Journal of Organic Chemistry, Год журнала: 2022, Номер 87(19), С. 12921 - 12931

Опубликована: Сен. 21, 2022

A simple visible-light-initiated strategy has been established for the construction of organophosphorus compounds via aerobic multicomponent reaction α-diazoesters, cyclic ethers, and P(O)H under air. number phosphonates phosphinates could be efficiently isolated in moderate to good yields without use photosensitizers metal reagents. This advantages mild condition, operation, eco-friendly energy, functional-group tolerance, gram-scale synthesis.

Язык: Английский

Процитировано

16
Light induced diversity-oriented synthesis (DOS) library of annulated indolizine fluorophores for imaging non-lysosomal lipid droplets (LDs) DOI
Debajit Maiti, Subrata Munan,

Shweta Singh

и другие.

Journal of Materials Chemistry B, Год журнала: 2023, Номер 11(10), С. 2191 - 2199

Опубликована: Янв. 1, 2023

DASS fluor (a novel annulated indolizines based fluorescent probe): their synthesis via DOS and biological evaluation for non-lysosomal LD detection.

Язык: Английский

Процитировано

7
Visible light-induced carbene reactivity of acceptor diazoalkanes: deconstructive difunctionalizations of cyclic ethers with nucleophiles DOI

Keyong Zhu,

Xinlong Zhou,

Yikun Ren

и другие.

Chemical Communications, Год журнала: 2022, Номер 59(5), С. 631 - 634

Опубликована: Дек. 6, 2022

A visible light-induced carbene reactivity of acceptor diazoalkanes has been developed for the synthesis difunctionalized ethers from cyclic and various N/O/S nucleophiles.

Язык: Английский

Процитировано

10