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

Pseudo‐Multicomponent Reactions of Lawsone: Synthetic Strategies of Bis‐Lawsone DOI Open Access
Swadhin Swaraj Acharya,

Dibyaranjan Samantaray,

Chipuru Sibakrishna

et al.

ChemistrySelect, Journal Year: 2025, Volume and Issue: 10(1)

Published: Jan. 1, 2025

Abstract 1,4‐Naphthoquinones (1,4‐NQs) are an important class of molecules with diverse pharmaceutical applications. Lawsone, a naturally occurring molecule range bioactivities, falls in the 1,4‐NQs. It possesses 1,3‐dicarbonyl functionality, which has been utilized synthesis bis‐lawsones reaction aldehydes. In this review we have discussed notable developments bis‐lawsone from 2009 to 2023. Also, highlights limitations and future perspectives area.

Language: Английский

Citations

1

Electrochemical Regioselective C(sp2)–H Selenylation and Sulfenylation of Substituted 2-Amino-1,4-naphthoquinones DOI
Pintu Karmakar, Indrajit Karmakar, D. R. PAL

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(2), P. 1049 - 1060

Published: Jan. 4, 2023

A straightforward and efficient electrochemical method for regioselective C(sp2)-H selenylation sulfenylation of substituted 2-amino-1,4-naphthoquinones has been unearthed. This oxidative cross-coupling reaction avoids using transition metal catalysts, oxidants, high temperatures. The other notable advantages this protocol are the tolerance diverse functional groups, mild conditions at ambient temperature, energy efficiency, good to excellent yields, short times (in minutes), gram-scale applicability, eco-friendliness.

Language: Английский

Citations

22

Rose‐Bengal‐Photocatalyzed Cross‐Dehydrogenative Coupling Reactions under Visible Light DOI

Divyani P. Patel,

Satish K. Singh

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(8)

Published: Jan. 19, 2024

Abstract Over the past few years, organic chemistry has used dye rose bengal‘s ability to absorb visible light. In present‐day research, innovation of environmentally friendly processes for carbon‐carbon/carbon‐heteroatoms (Nitrogen, Oxygen, Sulphur, and Phosphorus) bond formation great importance. The photocatalyzed cross‐dehydrogenative coupling (CDC) reactions using bengal (RB) is a promising technique creating carbon‐carbon/carbon‐heteroatom bonds directly from readily available compounds. Our review focuses on current advancement in that uses bond‐making synthesize various important molecules via CDC reactions.

Language: Английский

Citations

6

Photochemical and electrochemical regioselective cross-dehydrogenative C(sp2)–H sulfenylation and selenylation of substituted benzo[a]phenazin-5-ols DOI

Nayana Nayek,

Pintu Karmakar, Mullicka Mandal

et al.

New Journal of Chemistry, Journal Year: 2022, Volume and Issue: 46(28), P. 13483 - 13497

Published: Jan. 1, 2022

The essence of photo- and electrochemistry: sulfenylation selenylation substituted benzo[ a ]phenazin-5-ols through cross-dehydrogenative C(sp 2 )–H functionalization.

Language: Английский

Citations

19

Copper-Catalyzed Asymmetric Propargylic [3 + 2] Cycloaddition: Synthesis of Enantioenriched Dihydrofuro[3,2-c]coumarins and its Quinolinone and Thiocoumarin Analogues DOI

Shweta Rohilla,

Sadhna Shah,

Vinod K. Singh

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(20), P. 3733 - 3738

Published: May 16, 2023

A copper(II)-P,N,N-ligand catalyzed propargylic [3 + 2] cycloaddition approach for the synthesis of optically enriched dihydrofuro[3,2-c]coumarins has been accomplished first time. The utilizes esters as C2-bis-electrophiles and 4-hydroxycoumarin derivatives C,O-bis-nucleophiles. In addition, this novel strategy was also explored with 4-hydroxy-2-quinolinones 4-hydroxythiocoumarins. Moreover, various their quinolinone thiocoumarin analogues were synthesized in moderate to good yields high enantioselectivities.

Language: Английский

Citations

12

DFT investigation of the DDQ-catalytic mechanism for constructing C–O bonds DOI

Xiufang Zheng,

Da‐Gang Zhou, Lijun Yang

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(18), P. 3693 - 3707

Published: Jan. 1, 2024

The DDQ-catalytic mechanisms for constructing C–O bonds via H 2 O and CH 3 OH as oxygen sources have been investigated with DFT.

Language: Английский

Citations

4

Annulative Coupling of Sulfoxonium Ylides with Aldehydes and Naphthols or Coumarins: Easy Access to Fused Dihydrofurans DOI

Rahul Kumar Saini,

Paran J. Borpatra, Satyendra Kumar Pandey

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: 90(4), P. 1645 - 1655

Published: Jan. 17, 2025

We present a novel, metal- and additive-free method for the robust synthesis of dihydrofuran-fused naphthalenes coumarins. This approach utilizes annulative coupling sulfoxonium ylides with aldehydes, naphthols, or coumarins at ambient temperature. The exhibits broad substrate compatibility, accommodating various functional groups on naphthol coumarin derivatives resulting in good to high yields desired products. Additionally, we successfully scaled up reactions, synthesized were further converted other valuable bioactive molecules, validating viability our approach.

Language: Английский

Citations

0

Visible-Light-Induced Tandem Radical Brominative Addition/Cyclization of Activated Alkynes with CBr4 for the Synthesis of 3-Bromocoumarins DOI

Chenyang Yan,

Zhengwei Wu, Xiaoyu He

et al.

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 88(1), P. 647 - 652

Published: Dec. 8, 2022

A visible-light-induced tandem radical brominative addition/spiro-cyclization/1,2-ester migration of activated alkynes with CBr4 is developed. This protocol features good functional group tolerance, operational simplicity, and mild reaction conditions without the use catalysts external additives, providing easy access to valuable 3-bromocoumarins in generally high yields.

Language: Английский

Citations

14

Mechanochemical Solvent‐Free One‐Pot Synthesis of Poly‐Functionalized 5‐(Arylselanyl)‐1H‐1,2,3‐triazoles Through a Copper(I)‐Catalyzed Click Reaction DOI
Pintu Karmakar, Indrajit Karmakar, Debojyoti Mukherjee

et al.

Chemistry - A European Journal, Journal Year: 2023, Volume and Issue: 29(63)

Published: Sept. 4, 2023

A mechanochemistry-driven practical and efficient synthetic protocol for accessing diverse series of biologically relevant poly-functionalized 5-(arylselanyl)-1H-1,2,3-triazoles through copper(I)-catalyzed click reaction between aryl/heteroaryl acetylenes, diaryl diselenides, benzyl bromides, sodium azide has been accomplished under high-speed ball-milling. Advantages this method include operational simplicity, avoidance using solvent external heating, one-pot synthesis, short time in minutes, good to excellent yields, broad substrate scope, gram-scale applications. Furthermore, synthesized organoselenium compounds were synthetically diversified promising selenones.

Language: Английский

Citations

5

Electrorearranged Difunctionalization of 4-Hydroxy-α-benzopyrones DOI
Indrajit Karmakar, Goutam Brahmachari

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(15), P. 10524 - 10537

Published: July 19, 2024

We herein report the exploration of an electrosynthetic strategy as a highly efficient and straightforward alternative protocol for accessing diversely substituted biologically promising alkyl 2-hydroxy-3-oxo-2,3-dihydrobenzofuran-2-carboxylates through electrorearranged difunctionalization 4-hydroxycoumarins, involving singlet oxygen insertion from molecular oxygen, at ambient temperature. The present method is notably more advantageous than previously reported photochemical conversion regarding yields reaction times, substrate scope functional group tolerability, operational simplicity, scalability.

Language: Английский

Citations

1