Hypervalent Iodine(III)‐Catalysis Using Sulfoxide Oxidant for the Dehydrogenative Cycloisomerization‐Arylation Reaction of 2‐Propargyl 1,3‐Dicarbonyl Compounds DOI

Yuki Umakoshi,

Akira Tsubouchi, Akira Yoshimura

et al.

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

Published: Feb. 7, 2024

Abstract We report herein an unprecedented hypervalent iodine(III)‐catalysis using the activated sulfoxide. Since present catalytic systems promote dehydrogenative cycloisomerization‐arylation reaction of 2‐propargyl 1,3‐dicarbonyl compounds with aromatics, this also provides one few methods for iodine(III)‐catalyzed intermolecular carbon‐carbon bond formation aromatics.

Language: Английский

Visible-Light-Induced C (sp3)–H Functionalization of Tosylhydrazones: Synthesis of Polysubstituted Pyrroles under Metal-Free Conditions DOI
N. Naresh Kumar Reddy, Deepa Rawat, Subbarayappa Adimurthy

et al.

The Journal of Organic Chemistry, Journal Year: 2018, Volume and Issue: 83(16), P. 9412 - 9421

Published: July 19, 2018

Iodine catalyzed C (sp3)-H functionalization of tosylhydrazones with β-enamino esters under visible light irradiation for the synthesis trisubstituted pyrroles has been described. The present method is also applicable to α- substituted yield tetra-substituted pyrroles.

Language: Английский

Citations

22
I2-Promoted Multicomponent Dicyclization and Ring-Opening Sequences: Direct Synthesis of Benzo[e][1,4]diazepin-3-ones via Dual C–O Bond Cleavage DOI
Xiao Geng, Can Wang, Chun Huang

et al.

Organic Letters, Journal Year: 2019, Volume and Issue: 21(18), P. 7504 - 7508

Published: Sept. 5, 2019

A novel and efficient formal [4 + 2+1] annulation of aryl methyl ketones 2-aminobenzyl alcohols for the synthesis benzo[e][1,4]diazepin-3-ones is reported. This reaction successfully affords diverse seven-membered ring lactams via dual C–O bond cleavage. preliminary mechanistic study showed that a multicomponent dicyclization ring-opening sequence might occur, with introduction sulfide proposed as last step. strategy mild conditions broad substrate scope has potential applications in chemistry medicine.

Language: Английский

Citations

22
NaHS·nH2O-induced umpolung: the synthesis of 2-acyl-3-aminoindoles from aryl methyl ketones and 2-aminobenzonitriles DOI
Xiao Geng, Xia Wu, Can Wang

et al.

Chemical Communications, Journal Year: 2018, Volume and Issue: 54(90), P. 12730 - 12733

Published: Jan. 1, 2018

An efficient method for constructing 2-acyl-3-aminoindoles from methyl ketones and 2-aminobenzonitriles is described, in which NaHS·nH2O used as a novel umpolung reagent the first time organic synthesis.

Language: Английский

Citations

21
Reactions involving aryl methyl ketone and molecular iodine: a powerful tool in the one-pot synthesis of heterocycles DOI
Saideh Rajai‐Daryasarei, Mohammad Hossein Gohari, Narges Mohammadi

et al.

New Journal of Chemistry, Journal Year: 2021, Volume and Issue: 45(44), P. 20486 - 20518

Published: Jan. 1, 2021

The preparation of heterocyclic compounds has attracted great attention in organic chemistry because their extensive application the field bioactive molecules, materials science, and natural products.

Language: Английский

Citations

17
Hypervalent Iodine(III)‐Catalysis Using Sulfoxide Oxidant for the Dehydrogenative Cycloisomerization‐Arylation Reaction of 2‐Propargyl 1,3‐Dicarbonyl Compounds DOI

Yuki Umakoshi,

Akira Tsubouchi, Akira Yoshimura

et al.

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

Published: Feb. 7, 2024

Abstract We report herein an unprecedented hypervalent iodine(III)‐catalysis using the activated sulfoxide. Since present catalytic systems promote dehydrogenative cycloisomerization‐arylation reaction of 2‐propargyl 1,3‐dicarbonyl compounds with aromatics, this also provides one few methods for iodine(III)‐catalyzed intermolecular carbon‐carbon bond formation aromatics.

Language: Английский

Citations

2