Regioselective C₃Alkylation of Indoles for the Synthesis of Bis(indolyl)methanes and 3-Styryl Indoles

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(3), P. 1846 - 1857

Published: Jan. 12, 2024

Herein, we describe an efficient transition-metal-free regioselective C3alkylation of indoles for the synthesis bis(indolyl)methanes and 3-styryl indoles. Nitrobenzene is employed as oxidant to oxidize alcohols in presence a strong base reaction avoids use transition metals such Ru Mn. The protocol provides favorable route access biologically active compounds arundine, vibrindole A, turbomycin B.

Language: Английский

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Visible Light-Driven α-Diazoketones as Denitrogenated Synthons: Synthesis of Fluorinated N-Heterocycles via Multicomponent Cyclization Reactions

Organic Letters, Journal Year: 2023, Volume and Issue: 25(18), P. 3314 - 3318

Published: May 1, 2023

We disclose herein an efficient photochemical formal [3+2+1] annulation strategy for the transformation of diazocarbonyl compounds into various fluorinated nitrogen-containing heterocycles. This is characterized by reacting fluoroalkyl radicals with α-diazoketones, which are used as infrequent denitrogenated synthons under visible light. Moreover, a wide range N-heterocycles containing precious CF3 and perfluoroalkylated groups constructed in moderate to good yields. Notably, this may provide fruitful path synthesis complex organofluorides via diazo/fluorine/radical chemistry.

Language: Английский

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Chloride‐Promoted Photoelectrochemical C—H Silylation of Heteroarenes^†

Chinese Journal of Chemistry, Journal Year: 2023, Volume and Issue: 41(22), P. 2963 - 2968

Published: June 24, 2023

Comprehensive Summary A photoelectrochemical approach for the C—H silylation of heteroarenes through dehydrogenation cross‐coupling with H 2 evolution has been developed. The depends on hydrogen atom transfer (HAT) from silanes to Cl‐radical generated light‐induced homolytic cleavage Cl , in which was produced by electrochemical oxidation chloride. large number silylated heterocyclic molecules are rapidly constructed satisfactory yields without relying oxidants and metal reagents.

Language: Английский

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A general electron donor–acceptor complex enabled cascade cyclization of alkynes to access sulfur-containing heterocycles

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(8), P. 3111 - 3116

Published: Jan. 1, 2023

A general visible light-promoted and electron–donor–acceptor complex-enabled cascade reaction of alkynes to produce functionalized sulfur-containing heterocycles under photocatalyst-, base-, oxidant- metal-free conditions was developed.

Language: Английский

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Cu(ii)-catalyzed domino construction of spironaphthalenones by dearomatization of β-naphthols and using N,N-dimethylaminoethanol as a C1 synthon

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(15), P. 3101 - 3104

Published: Jan. 1, 2023

Herein, a Cu(II)-catalyzed facile construction of synthetically valuable spiro compounds from β-naphthols in air is reported, which N,N-dimethylaminoethanol (DMEA) serves as an efficient and unique C1 synthon. This transformation proceeds through ortho-quinone methide (o-QM) formation/Michael addition/dearomatization sequence, affording various spiro(naphthalenenaphtho)furan-2-ones moderate to excellent yields.

Language: Английский

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Copper-catalyzed divergent construction of naphthofurans and benzochromanes from 2-naphthols, 4-methylene-quinazolin(thi)ones, and N,N-dimethylethanolamine

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(4), P. 1198 - 1204

Published: Jan. 1, 2024

Cu( ii )-catalyzed divergent synthesis of naphthofurans and benzochromanes through [3 + 2 1] 1 annulations is established.

Language: Английский

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Metal-free construction of dihydropyrazino[2,3-b]indoles from 2-aminoacetophenones, isocyanates and 1,2-diamines

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(10), P. 2043 - 2048

Published: Jan. 1, 2024

A Brønsted acid/iodine co-mediated approach to construct dihydropyrazino[2,3-

Language: Английский

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Reductive thiolation and oxidative dehydroaromatization of cyclohexanones with primary amines and sodium sulfinates to access o-sulfanylanilines

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(21), P. 5484 - 5489

Published: Jan. 1, 2023

HI-promoted cascade reactions of cyclohexanones with primary amines and sodium sulfinates are described, providing an unprecedented method to access o -sulfanylanilines using as aryl source a sulfenylating reagent.

Language: Английский

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Photocatalytic C(sp²)–OMe bond cleavage and amidation of anisoles with N-hydroxyphthalimides and phthalimides

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(18), P. 4522 - 4528

Published: Jan. 1, 2023

The cleavage of the inert C(sp 2 )-OMe bond was developed under a metal-free photocatalytic strategy using 4CzIPN as mild oxidizing photoredox catalyst.

Language: Английский

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Cu(II)-catalyzed efficient construction of 1,3-naphthoxazines from 2-naphthols, amidines and N, N-dimethylethanolamine

Tetrahedron, Journal Year: 2023, Volume and Issue: 146, P. 133651 - 133651

Published: Sept. 13, 2023

Language: Английский

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