Visible‐Light‐Mediated Self‐Sensitized Oxidative and Regioselective C(sp2)−H Selenylation and Sulfenylation of Substituted 2‐Amino‐1,4‐Naphthoquinones DOI

Nayana Nayek,

Goutam Brahmachari

European Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 26(2)

Published: Dec. 2, 2022

Abstract A photochemical method based on visible‐light (white LEDs/sunlight) irradiation has been developed for the regioselective and oxidative C(sp 2 )−H selenylation sulfenylation of substituted 2‐amino‐1,4‐naphthoquinones under oxygen atmosphere. The process does not require any external photoredox catalysts. other notable advantages this protocol are metal‐free synthesis, visible light/sunlight as energy sources, good substrate scope, moderate to yields (41–91 %) with high regioselectivity.

Language: Английский

Erythrosine B Catalyzed Synthesis of trans-Dihydro-4H-furo[3,2-c]chromen-4-ones through Photocatalytic Dehydrogenative sp 3 C–O Bond Formation DOI
Avik Kumar Bagdi, Sourav Das,

Suvam Paul

et al.

Synthesis, Journal Year: 2023, Volume and Issue: 55(13), P. 2027 - 2036

Published: Feb. 9, 2023

Abstract A simple and efficient visible-light-induced methodology has been developed for the selective synthesis of dihydro-4H-furo[3,2-c]chromen-4-one derivatives via dehydrogenative coupling reaction. The is highly useful varieties dihydro-4H-furo[3,2-c]chromen-4-ones from readily accessible reactants under oxygen atmosphere. Importantly, additive-free approach also demonstrated this transformation. results mechanistic investigation showed that reaction proceeded through a radical pathway. Additionally, synthesized transformed into different 4H-furo[3,2-c]chromen-4-ones protocols.

Language: Английский

Citations

3

Boron Trifluoride Etherate-Controlled Reactions of Methyl Enol Ethers: Selective Synthesis of Dihydrofuro[3,2-c]chromenone and Furo[3,2-c]chromenone Derivatives DOI
Faiz Ahmed Khan,

Sarwat Asma Ziya Ahmad

Synlett, Journal Year: 2022, Volume and Issue: 34(07), P. 823 - 828

Published: July 28, 2022

Abstract A facile one-step synthetic approach to dihydrofuro-[3,2-c]chromenones and furo[3,2-c]chromenones by the reaction of methyl enol ethers with 4-hydroxycoumarins under metal-free conditions is presented. Dihydrofuro[3,2-c]chromenones furo[3,2-c]-chromenones were selectively obtained controlling stoichiometry boron trifluoride diethyl etherate. An unexpected aryl-group migration followed aromatization furan moiety, leading a variety furo[3,2-c]chromenone derivatives in good yields, reported.

Language: Английский

Citations

4

Practice of green chemistry strategies in synthetic organic chemistry: a glimpse of our sincere efforts in green chemistry research DOI
Goutam Brahmachari

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(63), P. 8153 - 8169

Published: Jan. 1, 2024

This feature article summarises our recent contributions (2019-2023) in designing and developing a handful of promising organic transformations for accessing several diversely functionalised biologically relevant scaffolds, following the green chemistry principles, particularly focusing on application low-energy visible light, electrochemistry, ball-milling, ultrasound, catalyst- additive-free synthetic strategies.

Language: Английский

Citations

0

Photo- and Electrochemical Organic Transformations Involving Radical Pathway: A Retrospection of Our Green-Chemistry-Inspired Synthetic Endeavours DOI
Goutam Brahmachari

Synlett, Journal Year: 2024, Volume and Issue: 35(20), P. 2273 - 2288

Published: July 8, 2024

Abstract This account summarises our recent efforts (2020 to mid-2024) in designing and developing a handful of promising organic transformations for accessing several diversely functionalized biologically relevant scaffolds by following the green-chemistry principles with particular focus on application low-energy visible light electrochemistry. Mechanistic studies each these reactions established involvement radical pathway. 1 Introduction 2 Green-Inspired Organic Transformations 2.1 Visible-Light-Driven Synthesis 2.1.1 Functionalized Dihydrofuro[3,2-c]chromenones 2.1.2 2-(Aryl/alkylamino)-3-(aryl/alkylselanyl)naphthalene-1,4-diones 2-(Arylamino)-3-(arylthio)naphthalene-1,4-diones 2.1.3 6-(Arylthio/arylseleno)benzo[a]phenazin-5-ols 2.1.4 3-(Alkyl/benzylthio)-4-hydroxy-2H-chromen-2-ones 2.1.5 2-Hydroxy-3-oxo-2,3-dihydrobenzofuran-2-carboxamides 2-Hydroxy-3-oxo-2,3-dihydrobenzofuran-2-carboxylates 2.1.6 2-Hydroxyphenylated α-Ketoamides 2.2 Electrochemical 2.2.1 3-Selenylated/Sulfenylated Derivatives 2-Amino-1,4-naphthoquinones 2.2.2 6-(Arylthio/Arylseleno)benzo[a]phenazin-5-ols 2.2.3 Alkyl 3 Conclusions

Language: Английский

Citations

0

Visible light–driven organic synthesis under Eosin Y photocatalysis DOI
Goutam Brahmachari

Elsevier eBooks, Journal Year: 2024, Volume and Issue: unknown, P. 91 - 149

Published: Aug. 16, 2024

Language: Английский

Citations

0

Visible light-driven organic synthesis: an introduction DOI
Goutam Brahmachari

Elsevier eBooks, Journal Year: 2024, Volume and Issue: unknown, P. 1 - 20

Published: Aug. 16, 2024

Language: Английский

Citations

0

Visible light–driven organic synthesis under Rose Bengal photocatalysis DOI
Goutam Brahmachari

Elsevier eBooks, Journal Year: 2024, Volume and Issue: unknown, P. 21 - 89

Published: Aug. 16, 2024

Language: Английский

Citations

0

Green synthetic approaches in organophosphorus chemistry: recent developments DOI
Goutam Brahmachari

Royal Society of Chemistry eBooks, Journal Year: 2024, Volume and Issue: unknown, P. 287 - 298

Published: Feb. 21, 2024

Organophosphorus chemistry is a broad and exciting field, with potential opportunities for researchers involved in multi-disciplinary areas of scientific endeavour, including organic, medicinal, pharmaceutical, agricultural, industrial chemistry. compounds find extensive applications all these fields owing to their inherent physical biological properties. Since its first development the 90s, green sustainable has grown considerably over past two decades. It become much more prevalent among working branches chemical science. As part noteworthy developments, synthetic organic chemists have been motivated develop eco-friendly methodologies generating phosphorus-functionalised interest, focusing on various principles. result, considerable progress towards accomplished during last decade. In continuation our earlier contributions, this chapter also aims offer an overview such developments approaches organophosphorus reported 2021.

Language: Английский

Citations

0

Electron Donor-Acceptor Complex Enabled Photocascade Strategy for Synthesis of trans-Dihydrofuro[3,2-c]chromen-4-one Scaffolds via Radical Conjugate Addition of Pyridinium Ylide DOI
Sovan Dey, Arindam Das, Ram Naresh Yadav

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

A photocascade strategy is disclosed for the synthesis of trans -dihydrofurocoumarin utilising EDA complex followed by 1,4-radical conjugate addition pyridinium ylide.

Language: Английский

Citations

0

Visible-light-induced intramolecular C–S bond formation for practical synthesis of 2,5-disubstituted 1,3,4-thiadiazoles DOI

Zhaocheng Shi,

Ruohan Li,

Wenqing Lan

et al.

Synthetic Communications, Journal Year: 2022, Volume and Issue: 53(1), P. 40 - 48

Published: Nov. 29, 2022

A general and facile visible-light mediated protocol for the synthesis of 2-arylamino-5-aryl-1,3,4- thiadiazoles via one-pot condensation intramolecular C–S coupling cascade reaction has been developed. This is mild, practical, metal-free exogenous oxidant-free, only involves Eosin Y as photocatalyst using oxygen sole terminal oxidant. exhibits synthetic simplicity, broad scope substrates, excellent functional group compatibility. Gram-scale can be also facilitated with a satisfactory yield, which opens up possibility practical applications.

Language: Английский

Citations

2