Cyanation with isocyanides: recent advances and perspectives

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(12), P. 1546 - 1562

Published: Jan. 1, 2024

This review focuses on the cyanation of isocyanides with recent advances and perspectives.

Language: Английский

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Mechanosynthesis of Pyrrole-2-carboxylic Acids via Copper-Catalyzed Spiroannulation/Ring-Opening Aromatization of 4-Arylidene Isoxazol-5-ones with Enamino Esters

Organic Letters, Journal Year: 2024, Volume and Issue: 26(20), P. 4189 - 4193

Published: May 14, 2024

An efficient and practical tandem reaction of 4-arylidene isoxazol-5-ones with enamino esters catalyzed by an inexpensive copper salt has been established in a ball mill. This innovative approach yields diverse array structurally novel pyrrole-2-carboxylic acids, showing excellent tolerance toward different functional groups. By integrating spiroannulation ring-opening aromatization processes, this protocol introduces facile cost-effective strategy for synthesizing highly functionalized pyrrole derivatives.

Language: Английский

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Tunable Synthesis of 4-Acyl- and 4-Formyl Pyrroles by Rhodium-Catalyzed Ring-Expansion of Azirines with Enaminones

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

Published: Feb. 19, 2025

A rhodium-catalyzed annulation of 2H-azirines with enaminones is presented. This protocol affords a convenient approach to the diversity-oriented synthesis 4-acyl- and 4-formyl pyrroles good functional group tolerance. The utility this reaction has been demonstrated by scale-up preparation, late-stage modification natural molecules, diverse derivatives.

Language: Английский

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C–H functionalization enabled by multiple isocyanides

Chemical Society Reviews, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

This review outlines in detail strategies for state-of-the-art synthetic routes and demonstrates various interactions from the synergistic combination of C–H functionalization with multiple isocyanides to establish complicated reactions.

Language: Английский

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Rh-catalysed divergent synthesis of polysubstituted pyrroles from α,β-unsaturated ketones via selective single or double insertion of isocyanides

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(22), P. 5559 - 5567

Published: Jan. 1, 2023

A novel divergent synthetic method for polysubstituted pyrroles from isocyanides and α,β-unsaturated ketones in the presence of a rhodium catalyst bis(pinacolato)diboron (B 2 pin ) is described here.

Language: Английский

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Hydrogen bond-promoted regio- and stereoselective synthesis of isoindoline derivatives through Pd-catalyzed isocyanide insertion reaction involving aziridines

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(6), P. 1775 - 1781

Published: Jan. 1, 2024

We have successfully demonstrated an efficient and practical Pd-catalyzed reaction between aziridine isocyanide, leading to the synthesis of isoindoline derivatives in moderate good yields.

Language: Английский

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[1,2]‐Phospha‐Brook Rearrangement‐Initiated Palladium‐Catalyzed Cyclization Reaction of Isocyanides and o‐Bromobenzaldehydes: Access to 2H‐Isoindole‐1‐carboxamides and 2H‐Isoindole‐1‐carbonitriles

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 20, 2024

Comprehensive Summary Herein, a [1,2]‐phospha‐Brook rearrangement‐initiated palladium‐catalyzed cyclization reaction for base‐controlled selective synthesis of 2 H ‐isoindole‐1‐carboxamide and ‐isoindole‐1‐carbonitrile derivatives has been described. This strategy features double isocyanide insertion, efficient bond combinations, simple operation conditions. Mechanistic studies show that the rearrangement is key step in this reaction. protocol offers novel concise ‐isoindole derivatives.

Language: Английский

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Solvent-involved synthesis of pyrrolidin-5-one-2-carboxamides via a sequential Ugi/olefination reaction

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(10), P. 2780 - 2785

Published: Jan. 1, 2024

An unprecedented multi-component reaction with solvent participation and a novel conversion of sulfur ylides was developed via Ugi/olefination to construct pyrrolidin-5-one-2-carboxamides.

Language: Английский

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Design and synthesis of tetrazole-linked quinazoline derivatives and their bioactivities against Microcystis aeruginosa FACHB905

Tetrahedron Letters, Journal Year: 2024, Volume and Issue: 140, P. 155046 - 155046

Published: April 1, 2024

Language: Английский

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Electro-oxidative three-component cascade coupling of isocyanides with elemental sulfur and amines for the synthesis of 2-aminobenzothiazoles

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(18), P. 3752 - 3760

Published: Jan. 1, 2024

2-Aminobenzothiazoles are commonly encountered in various functional compounds. Herein, we disclose an electro-oxidative three-component reaction for the effective synthesis of 2-aminobenzothiazoles under mild conditions, utilizing non-toxic and abundant elemental sulfur as source. Both aliphatic amines aryl demonstrate good compatibility at room temperature, highlighting broad group tolerance this approach. Additionally, selenium demonstrated reactivities comparable to those sulfur.

Language: Английский

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