Single-atom skeletal editing of 2H-indazoles enabled by difluorocarbene

Science China Chemistry, Journal Year: 2023, Volume and Issue: 66(7), P. 1975 - 1981

Published: May 11, 2023

Language: Английский

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Difluorocarbene-Mediated Trimethylsilylation of Nucleophiles with HCF₂N(TMS)₂ as a Silylation Reagent

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 10, 2025

Described herein is the trimethylsilylation of various nucleophiles using a combination HCF3 and NaHMDS. This facile protocol enables rapid construction alkynylsilanes, silyl enol ethers, etc., under mild conditions. Detailed mechanistic studies indicate that trimethylsilicon intermediate formed in situ can be readily attacked by nucleophiles, with activation base NaHMDS difluorocarbene. work first utilizes structure HMDS as silicon source terminal alkynes.

Language: Английский

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Difluorocarbene-Enabled Dehydration of Primary Amides To Access Nitriles

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: March 16, 2025

A cost-effective and environmentally friendly method for the direct conversion of primary amides to nitriles was developed using commercially available non-toxic ethyl bromodifluoroacetate as a difluorocarbene precursor under metal-free ligand-free conditions. The reaction features high yields tolerates various sensitive moieties, including alkyl, alkenyl, ether, sulfone, sulfoxide, heteroaryl, chloro, bromo, iodo, hydroxyl, nitro, cyano groups, late-stage modification complex molecules is also feasible. Moreover, present effective on large scales, showing potential industrial application.

Language: Английский

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C–F bond functionalizations via fluorinated carbenes

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(22), P. 5782 - 5804

Published: Jan. 1, 2023

This feature article summarizes the developments in fluorinated carbene transformations, and their consequent C–F functionalization a cascade platform.

Language: Английский

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TBD-Mediated Diastereoselective Access to Functionalized 3-Alkenyl-2-oxindoles via the Tandem Reaction of Isatins and Allenoates

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(19), P. 14021 - 14027

Published: Sept. 20, 2024

The 1,5,7-triazabicyclo[4.4.0]dec-5-ene-mediated tandem reaction of easily accessible isatins and allenoates to functionalized 3-alkenyl-2-oxindoles is disclosed. allows the synthesis a wide range in good yields with excellent functional group tolerance under mild conditions (32 examples, up 84% yields). current strategy will provide novel path for sustainable 3-alkenyl-2-oxindole derivatives. We have also demonstrated significance as key starting materials (KSMs) via their synthetic utility producing oxindole-appended pyrazole, oxazole, coumarin hybrids medicinal relevance.

Language: Английский

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Regio- and diastereoselective synthesis of thioxothiazolidin-indolin-2-ones, oxoindolin-carbamodithioate hybrids, and their base-catalyzed conversion into dispirocyclopentanebisoxindoles

Scientific Reports, Journal Year: 2024, Volume and Issue: 14(1)

Published: June 20, 2024

Abstract In this publication, we reported a regio-, diastereoselective, and kinetically controlled reaction for synthesizing thioxothiazolidin-indolin-2-ones, oxoindolin-carbamodithioate hybrids, their base-catalyzed conversion into dispirocyclopentanebisoxindoles. Obtaining only the kinetic thioxothiazolidin-indolin-2-one products together with straightforward to dispirocyclopentanebisoxindoles, excellent regio- diastereoselectivity, easy workup, one-pot synthetic operation are considerable advantages of work.

Language: Английский

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Difluorocarbene as a C–F source for the construction of fluorinated benzothiazoles

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 11(1), P. 120 - 126

Published: Nov. 13, 2023

Described herein is the use of difluorocarbene as a C–F source for cyclization 2-aminobenzenethiols to provide fluorinated benzothiazoles. A one-step process installs fluorine atom and constructs heterocycle.

Language: Английский

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Thiocarbonyl fluoride generated in situ from difluorocarbene for cyclization of vicinal X-H substituted amines (X = N, O or S)

Journal of Fluorine Chemistry, Journal Year: 2023, Volume and Issue: 272, P. 110212 - 110212

Published: Nov. 1, 2023

Language: Английский

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Difluorocarbene-based Trifluoromethylthiolation of Aryl and Alkenyl Iodides

Acta Chimica Sinica, Journal Year: 2024, Volume and Issue: 82(2), P. 115 - 115

Published: Jan. 1, 2024

Language: Английский

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Regio- and diastereoselective synthesis of thioxothiazolidin- indolin-2-ones, oxoindolin-carbamodithioate hybrids, and their base-catalyzed conversion into dispirocyclopentanebisoxindoles

Research Square (Research Square), Journal Year: 2024, Volume and Issue: unknown

Published: May 15, 2024

In this publication, we reported a regio-, diastereoselective, and kinetically controlled reaction for synthesizing thioxothiazolidin-indolin-2-ones, oxoindolin-carbamodithioate hybrids, their base-catalyzed conversion into dispirocyclopentanebisoxindoles. Obtaining only the kinetic thioxothiazolidin-indolin-2-one products together with straightforward to dispirocyclopentanebisoxindoles, excellent regio- diastereoselectivity, easy workup, one-pot synthetic operation are considerable advantages of work.

Language: Английский

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