Cascade in Situ Iodination, Chromone Annulation, and Cyanation for Site-Selective Synthesis of 2-Cyanochromones

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(6), P. 4017 - 4023

Published: March 2, 2023

A facile cascade reaction for the site selective synthesis of 2-cyanochromones is described. By using simple o-hydroxyphenyl enaminones and potassium ferrocyanide trihydrate (K4[Fe(CN)6]3·3H2O) as starting materials I2/AlCl3 promoters, products are furnished via tandem chromone ring formation C–H cyanation. The in situ 3-iodochromone a formal 1,2-hydrogen atom transfer (HAT) process account unconventional selectivity. In addition, 2-cyanoquinolin-4-one has been realized by employing corresponding 2-aminophenyl enaminone substrate.

Language: Английский

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Optoelectronic properties and charge transfer dynamics in graphene quantum dot/Ir(III) nanocomposites: Enhancing photocatalytic performance through strategic BTF conjugate binding and end-capping variations

Diamond and Related Materials, Journal Year: 2024, Volume and Issue: 145, P. 111107 - 111107

Published: April 17, 2024

Language: Английский

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An update on the advances in chromone and the derivatives synthesis based on the key chromone annulation of o-hydroxyaryl enaminones

Chinese Chemical Letters, Journal Year: 2024, Volume and Issue: unknown, P. 110784 - 110784

Published: Dec. 1, 2024

Language: Английский

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Synthesis of difluoromethyl carbinols from the Friedel–Crafts reaction of electron-rich arenes with difluorovinyl arylsulfonates

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(22), P. 6273 - 6280

Published: Jan. 1, 2022

An efficient, sustainable and straightforward method is reported for the synthesis of a series α,α-difluoromethyl carbinols via K 2 CO 3 -triggered Friedel–Crafts reaction electron-rich arenes using stable easily affordable 2,2-difluorovinyl arylsulfonate.

Language: Английский

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Rh(III)-Catalyzed Oxidative C–H Activation/Annulation of Salicylaldehydes with Masked Enynes for the Synthesis of Chromones

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 88(1), P. 548 - 558

Published: Dec. 20, 2022

A rhodium(III)-catalyzed oxidative C–H activation/annulation of salicylaldehydes with propargylic acetates has been developed for the regioselective synthesis 3-vinyl chromones in good yields broad functional group tolerance. 3-Vinyl were converted into biologically active benzo[c]xanthone by I2-mediated electrocyclization.

Language: Английский

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Vinyl Esters and Vinyl Sulfonates as Green Alternatives to Vinyl Bromide for the Synthesis of Monosubstituted Alkenes via Transition-Metal-Catalyzed Reactions

Chemistry, Journal Year: 2023, Volume and Issue: 5(4), P. 2288 - 2321

Published: Oct. 20, 2023

This review summarizes the applications of vinyl sulfonate and acetate as green alternatives for bromide in cross-coupling reactions. In first part, preparation sulfonates their reactions are briefly discussed. Then, a brief reactions, including cyclization Fujiware–Moritani reaction, transvinylation described.

Language: Английский

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Rh(iii)-catalyzed redox-neutral C–H alkenylation of benzamides with gem-difluorohomoallylic silyl ethers via β-H elimination

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(25), P. 3747 - 3750

Published: Jan. 1, 2023

Fluorinated molecules are widely used in pharmaceutical and agrochemical industries. Herein we report the synthesis of 2-(3,3-difluoro-4-(silyloxy)but-1-en-1-yl)benzamides from unprecedented rhodium(III)-catalyzed alkenylation various benzamides with difluorohomoallylic silyl ethers. The practicability this protocol is demonstrated by its broad substrate compatibility, good functional group tolerance, ready scalability high regioselectivity. oxygen ethers makes β-H elimination feasible, which suppresses both β-F dialkenylation benzamides. This redox-neutral reaction proceeds efficiently via N-O bond cleavage without external oxidants thus provides new opportunities for elaborate difluorinated compounds readily available fluorinated synthons.

Language: Английский

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Assembly of fluorinated benzodiazepines via Rh(iii)-catalysed [5+2] annulation of N-benzo[d]imidazole indolines with 2,2-difluorovinyl tosylate

New Journal of Chemistry, Journal Year: 2023, Volume and Issue: 47(27), P. 12589 - 12594

Published: Jan. 1, 2023

Solvent-tunable Rh( iii )-catalysed C–H activation/[5+2] annulation of N -benzo[ d ]imidazole indolines with 2,2-difluorovinyl tosylate was realized for building monofluorinated and gem -difluorinated benzodiazepines.

Language: Английский

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Rh(III)-Catalyzed, Redox-Neutral, C–H Multifluoroalkenylation of Benzamides

Synthesis, Journal Year: 2024, Volume and Issue: 56(19), P. 3045 - 3053

Published: June 11, 2024

Abstract Fluorinated molecules are widely used in pharmaceutical and agrochemical industries. Multifluoroalkyl-containing compounds have attracted increasing attention for their unique ability to alter the activity of drugs bioactive molecules. Herein, we report an efficient Rh(III)-catalyzed, redox-neutral, C–H multifluoroalkenylation benzamides with multifluoroalkenes, which provides a versatile protocol accessing wide range multifluoroalkenylated arenes.

Language: Английский

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The Construction of Multifarious Monofluoroalkene Derivatives from 2H‐imidazoles via a Three‐Component Coupling

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(13), P. 2225 - 2229

Published: June 14, 2023

Abstract A Rh(III)‐catalyzed three‐component coupling reaction for the regioselective assembly of various monofluoroalkene derivatives was disclosed using readily available difluorovinyl tosylates as fluorinated partners. This strategy intended preparation fluorovinyl heterocycles, and main OTs intermediates could be further processed to alkenyl compounds.

Language: Английский

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