Ring-Opening Selenation of Cyclopropanol for the Selective Synthesis of β-Hydroxy-Substituted Selenylated Ketones

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(21), P. 14685 - 14694

Published: Oct. 7, 2022

Ring opening of cycloalkanols has been employed as a commonly used strategy to prepare diverse distal functionalized ketones. However, most these ketones obtained by this belong monofunctional ketones, while difunctional with more potential application value have rarely reported. Herein, we first reported mild I2-promoted ring-opening selenation cyclopropanol synthesize various In the reaction, hydroxyl (−OH) derived from water and RSe+ diselenide can be introduced into α- β-positions, respectively, delivering β-hydroxy selenylated in good excellent yields.

Language: Английский

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Organophotocatalytic Remote Thiocyanation Reaction via Ring‐Opening Functionalization of Cycloalkanols

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(36)

Published: April 18, 2024

The remote C(sp

Language: Английский

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Ring-Opening Coupling of Cyclopropanol with 1,2,3-Triazole for the Synthesis of Fused Triazoles

Organic Letters, Journal Year: 2024, Volume and Issue: 26(19), P. 4043 - 4048

Published: May 2, 2024

A radical ring-opening arylation of cyclopropanol with 1,2,3-triazole has been achieved. This synthetic protocol provides straightforward access to a wide range structurally diverse and chiral 4,5,6,7-tetrahydro[1,2,3]triazolo[1,5-a]pyridines high efficiency from readily available cyclopropanols.

Language: Английский

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Divergent Synthesis of β-Fluoroamides via Silver-Catalyzed Oxidative Deconstruction of Cyclopropanone Hemiaminals

Organic Letters, Journal Year: 2023, Volume and Issue: 25(28), P. 5389 - 5394

Published: July 6, 2023

An expedient approach for the synthesis of challenging β-fluoroamides from readily accessible cyclopropanone equivalents is reported. Following addition pyrazole used here as a transient leaving group, silver-catalyzed regiospecific ring-opening fluorination resulting hemiaminal leads to β-fluorinated

Language: Английский

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Brønsted Acid‐Catalyzed Markovnikov Hydroarylation of Arylcyclobutene: A Route to gem‐Diaryl‐Substituted Cyclobutanes

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(12), P. 2705 - 2709

Published: May 4, 2024

Abstract A regioselective Markovnikov hydroarylation of arylcyclobutene has been developed using Brønsted acid catalysis through a protonation/Friedel‐Crafts sequence. The metal‐free catalytic reaction is operationally simple and feasible compared to previous reports that utilized elaborate specific polyfluorinated reagents, affording variety gem ‐diaryl‐ substituted in good yields. possible mechanism the explored step‐by‐step control experiments. This protocol involving indole ‐diaryl‐substituted cyclobutene scaffolds not only enriches applications catalyzed hydroarylation, but also paves way for more extensive access potential bioactive cyclobutanes structures.

Language: Английский

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An organophotoredox-catalyzed C(sp²)–N cross coupling reaction of cyclic aldimines with cyclic aliphatic amines

Organic & Biomolecular Chemistry, Journal Year: 2021, Volume and Issue: 19(16), P. 3595 - 3600

Published: Jan. 1, 2021

An organophotocatalyzed C(sp2)-H/N-H cross-dehydrogenative coupling of cyclic aldimines with aliphatic amines has been developed, which represents the first example visible-light-induced C-H amination N-sulfonylated imines. This methodology enables streamline assembly amine derivatives via radical mediated C-N bond formation. The current protocol features transition-metal-free, mild conditions, good functional group tolerance and yields.

Language: Английский

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Silver-catalyzed cyclization of α-imino-oxy acids to fused tetralone derivatives

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(13), P. 2700 - 2704

Published: Jan. 1, 2023

A silver-catalyzed cyclization of α-imino-oxy acids under mild conditions has been described. This reaction offers facile access to a diverse range fused tetralone derivatives with exquisite stereoselectivity in moderate good yields.

Language: Английский

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Lewis-Acid-Catalyzed Tandem Cyclization by Ring Expansion of Tertiary Cycloalkanols with Propargyl Alcohols

Organic Letters, Journal Year: 2021, Volume and Issue: 23(24), P. 9457 - 9462

Published: Dec. 3, 2021

A new method for the efficient synthesis of hexahydro-1H-fluorene and octahydrobenzo[a]azulene derivatives through a ring-expansion strategy is reported. With an appropriate combination thulium(III) trifluoromethanesulfonate 13X molecular sieves, range unsaturated polycyclic compounds were obtained in good yields. Mechanism studies reveal that reaction more likely to undergo Meyer-Schuster rearrangement, ring expansion, Friedel-Crafts-type pathways, which provide conceptually different opening tertiary cycloalkanols.

Language: Английский

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Photoinduced decatungstate-catalyzed direct coupling of cycloalkanes and cyclic aldimines

Green Synthesis and Catalysis, Journal Year: 2023, Volume and Issue: unknown

Published: Oct. 1, 2023

We first describe a photoinduced decatungstate-catalyzed direct coupling of cycloalkanes and cyclic aldimines. The desired products were generated in moderate to good yields with wide substrate scope under mild reaction conditions. mechanistic study revealed radical process. In addition, the usefulness organic synthesis was proved by scale-up as well late-stage modification drug-like molecules.

Language: Английский

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CeCl₃-Catalyzed C–H Alkylation of N-Sulfonyl Ketimines with Alkanes and Ether via Photoinduced Ligand-to-Metal Charge Transfer

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(24), P. 18337 - 18343

Published: Dec. 9, 2024

A cerium-catalyzed C–H alkylation of N-sulfonyl ketimines with low-cost and readily available alkanes as alkyl sources was developed. This transformation proceeded through the synergy photoinitiated ligand-to-metal charge transfer (LMCT) using a chlorine radical an HAT reagent air green oxidant. series alkylated were synthesized moderate to good yields in highly atom-economic manner under chemical oxidant-free conditions.

Language: Английский

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