HFIP in Organic Synthesis

Chemical Reviews, Journal Year: 2022, Volume and Issue: 122(15), P. 12544 - 12747

Published: July 17, 2022

1,1,1,3,3,3-Hexafluoroisopropanol (HFIP) is a polar, strongly hydrogen bond-donating solvent that has found numerous uses in organic synthesis due to its ability stabilize ionic species, transfer protons, and engage range of other intermolecular interactions. The use this exponentially increased the past decade become choice some areas, such as C–H functionalization chemistry. In review, following brief history HFIP an overview physical properties, literature examples reactions using or additive are presented, emphasizing effect each reaction.

Language: Английский

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Rh(III)-Catalyzed [5 + 1] Annulation of Indole-enaminones with Diazo Compounds To Form Highly Functionalized Carbazoles

Organic Letters, Journal Year: 2021, Volume and Issue: 23(11), P. 4406 - 4410

Published: May 21, 2021

A novel Rh(III)-catalyzed C–H activation/annulation cascade of indole-enaminones with diazo compounds was reported to construct diversely functionalized carbazole frameworks. The most notable characteristic is that this transformation could smoothly furnish a [5 + 1] cyclization product good excellent yields (up 95%), accompanied by the thorough removal acetyl and N,N-dimethyl groups two substrates from target products, rather than normally expected [4 2] products.

Language: Английский

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Rh(III)-Catalyzed Spiroannulation Reaction of N-Aryl Nitrones with 2-Diazo-1,3-indandiones: Synthesis of Spirocyclic Indole-N-oxides and Their 1,3-Dipolar Cycloaddition with Maleimides

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(6), P. 3845 - 3858

Published: March 8, 2023

An efficient strategy for the preparation of spirocyclic indole-N-oxide compounds through a Rh(III)-catalyzed [4 + 1] spiroannulation reaction N-aryl nitrones with 2-diazo-1,3-indandiones as C1 synthons under extremely mild conditions is presented. From this reaction, 40 indole-N-oxides were easily obtained in up to 98% yield. In addition, title could be successfully used construction structurally intriguing maleimide-containing fused polycyclic scaffolds via diastereoselective 1,3-dipolar cycloaddition maleimides.

Language: Английский

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Synthesis of Pyrazolo[1,2‐a]cinnolines via Rhodium(III)‐Catalyzed [4+2] Annulation Reactions of Pyrazolidinones with Sulfoxonium Ylides

Advanced Synthesis & Catalysis, Journal Year: 2021, Volume and Issue: 363(13), P. 3311 - 3317

Published: May 8, 2021

Abstract A method to synthesize pyrazolo[1,2‐a]cinnolines via rhodium(III)‐catalyzed C−H activation of pyrazolidinones and subsequent [4+2] annulation sulfoxonium ylides was developed. 5‐Substituted or 5,10‐disubstituted could be obtained by slightly adjusting the reaction conditions. Gram‐scale synthesis practical transformations proved practicability this method. The mechanism proposed in article on basis preliminary mechanistic results previous reports. This features simplified operation, metal‐oxidant free, readily available reactants. magnified image

Language: Английский

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Novel Sulfinamide-Based Chiral Ligand Promoted Chiral Diarylmethanol Preparation via exo-Directed Asymmetric C–H Alkynylation under Mild Conditions

ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 2540 - 2549

Published: Jan. 28, 2025

Language: Английский

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Pyran-Fused Analogues and Their Potential Applications

Russian Journal of Bioorganic Chemistry, Journal Year: 2025, Volume and Issue: 51(2), P. 373 - 438

Published: April 1, 2025

Language: Английский

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A removable directing group-assisted Rh(iii)-catalyzed direct C–H bond activation/annulation cascade to synthesize highly fused isoquinolines

Organic Chemistry Frontiers, Journal Year: 2020, Volume and Issue: 7(20), P. 3186 - 3192

Published: Jan. 1, 2020

A removable directing group-assisted Rh(iii)-catalyzed direct C–H bond activation/annulation cascade was developed to synthesize highly fused isoquinolines with good excellent yields and a functional group tolerance.

Language: Английский

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Sulfoximines Assisted Rh(III)-Catalyzed C–H Activation/Annulation Cascade to Synthesize Highly Fused Indeno-1,2-benzothiazines

The Journal of Organic Chemistry, Journal Year: 2021, Volume and Issue: 86(21), P. 15217 - 15227

Published: Oct. 6, 2021

A facile access to highly fused tetracyclic indeno-1,2-benzothiazines has been established via a Rh(III)-catalyzed C-H bond activation and intramolecular annulation cascade between sulfoximides all-carbon diazo indandiones. This strategy is characterized by the fact that coupling partners do not require preactivation, along with its high efficiency, broad substrate generality, transformation. Particularly, conjugated products demonstrate good optical properties can easily enter cells emit bright fluorescence for live cell imaging.

Language: Английский

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Synthesis of 8-Alkoxy-5H-isochromeno[3,4-c]isoquinolines and 1-Alkoxy-4-arylisoquinolin-3-ols through Rh(III)-Catalyzed C–H Functionalization of Benzimidates with 4-Diazoisochroman-3-imines and 4-Diazoisoquinolin-3-ones

The Journal of Organic Chemistry, Journal Year: 2020, Volume and Issue: 85(8), P. 5525 - 5535

Published: March 23, 2020

Rh(III)-catalyzed C-H activation/annulation of benzimidates with 4-diazoisochroman-3-imines furnished 8-alkoxy-5H-isochromeno[3,4-c]isoquinolines in moderate to excellent yields a broad range substrate scope. The reaction was carried out under mild conditions and could be scaled up practical usage. Similar between 4-diazoisoquinolin-3-ones provided 1-alkoxy-4-arylisoquinolin-3-ols yields. Moreover, the synthesized products conveniently transformed corresponding heterocycles 1,8-naphthyridinone or isochromenopyridinone core, which are privileged structures medicinal chemistry.

Language: Английский

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Rh(III)-Catalyzed Domino [4 + 2] Annulation/Aza-Michael Addition of N-(Pivaloyloxy)benzamides with 1,5-Enynes via C–H Activation: Synthesis of Functionalized Aromathecins

The Journal of Organic Chemistry, Journal Year: 2020, Volume and Issue: 85(12), P. 7905 - 7915

Published: May 21, 2020

Reported herein are the Rh(III)-catalyzed cascade annulation reactions of N-(pivaloyloxy)benzamides with 1,5-enynes to access diversely substituted aromathecin derivatives involving C-H activation. The developed procedure offers an efficient synthetic tool for assembly a wide range and good atom economy functional group tolerance. key involved in this alkyne insertion aza-Michael addition under oxidant-free mild reaction conditions.

Language: Английский

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