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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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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Visible-Light-Promoted Intermolecular β-Acyl Difunctionalization of Alkenes via Oxidative Radical-Polar Crossover

Organic Letters, Journal Year: 2023, Volume and Issue: 25(45), P. 8067 - 8071

Published: Nov. 8, 2023

A visible-light-induced β-acyl difunctionalization of alkenes with acyl oxime esters and various nucleophiles was developed to achieve molecular complexity from readily available raw materials via oxidative radical-polar crossover. variety nucleophiles, including NH-sulfoximines, indoles, indazole, trimethoxybenzene, were all effectively applicable the sustainable reaction system. The novel synthetic strategy features mild conditions, a broad substrate scope (39 examples), easy scale-up, excellent regioselectivity.

Language: Английский

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Divergent Trideuteromethylthiolation and Aminotrideuteromethylthiolation of Alkenes with N-Fluorobenzenesulfonimide and CD₃SSO₃Na

Organic Letters, Journal Year: 2023, Volume and Issue: 25(39), P. 7078 - 7082

Published: Sept. 21, 2023

A metal-free oxidative trideuteromethylthiolation of alkenes with CD3SSO3Na using NFSI as an oxidant has been developed. The aminotrideuteromethylthiolation a three-component reaction could be easily achieved in the presence cobalt catalyst. divergent alkenes, readily available reagent, and versatile synthetic strategy allow for late-stage modification drug molecules.

Language: Английский

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Electrochemical aminotrideuteromethylthiolation of isocyanides with anilines and CD₃SSO₃Na

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(15), P. 4264 - 4268

Published: Jan. 1, 2024

Herein, we describe an electrochemical strategy that enables the aminotrideuteromethylthiolation of isocyanides with anilines and CD 3 SSO Na, providing unprecedented route to access S -CD isothioureas in satisfactory yields.

Language: Английский

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Aminothiolation of alkenes with azoles and Bunte salts

Frontiers in Chemistry, Journal Year: 2024, Volume and Issue: 11

Published: Jan. 22, 2024

We have developed an intermolecular aminothiolation of simple olefins using Bunte salt as a thiolating agent. This protocol produces thiyl free radicals under PIDA oxidation conditions, eliminating the need for transition-metal catalysts. The method has wide range substrate applicability and is suitable large-scale preparation late-stage modification drug molecules.

Language: Английский

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Copper-catalyzed sulfonylation of alkenes with CH3SSO3Na

BMC Chemistry, Journal Year: 2025, Volume and Issue: 19(1)

Published: Feb. 22, 2025

A successful methodology for the copper-catalyzed dehydrogenated methylsulfonylation of alkenes utilizing CH3SSO3Na in conjunction with hypervalent iodine reagents was successfully established. This method offers a practical avenue to obtain allyl methyl sulfones and alkenyl by forming C-S bonds. Using C-H bond oxidation sulfonylation strategy Bunte salts, we synthesized total twenty two compounds, including four examples deuterium-substituted molecules, demonstrated one example scale-up reaction.

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 [2+2+m] Cyclization of 2‐Cyanoaryl Acrylamides with 2‐Bromocarbonyls Involving C(sp³)−H Functionalization

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(24), P. 4513 - 4519

Published: Oct. 31, 2023

Abstract An oxidant‐free photocatalytic [2+2+m] cyclization of 2‐cyanoaryl acrylamides with 2‐bromocarbonyls is reported, enabling the assembly biologically important N‐heterocycle‐fused quinolinones including benzo[1,6]naphthyridinones and pyrrolo[3,2‐ c ]‐quinolines. This protocol proceeds through a radical relay pathway alkene difunctionalization along an intramolecular cyano insertion subsequent site‐specific functionalization inert C( sp 3 )−H bond enabled by cyano‐derived iminyl radical‐mediated 1,n‐hydrogen atom transfer. Notably, this transformation selectively formed two distinct C−C bonds, one C−N bond, quaternary carbon center in one‐pot procedure.

Language: Английский

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