Electrochemical difunctionalization of alkenes and alkynes for the synthesis of organochalcogens involving C–S/Se bond formation

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 11(2), P. 597 - 630

Published: Nov. 23, 2023

This review highlights the recent progress in electrochemical difunctionalization of alkenes and alkynes involving C–S/Se bond formation to access organochalcogen frameworks.

Language: Английский

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Regioselective synthesis of 4-functionalized pyridines

Chem, Journal Year: 2023, Volume and Issue: 10(2), P. 628 - 643

Published: Nov. 21, 2023

Language: Английский

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Dative Bonding Activation Enables Precise Functionalization of the Remote B–H Bond of nido-Carborane Clusters

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 13, 2024

The innovation of synthetic strategies for selective B-H functionalization is a pivotal objective in the realm boron cluster chemistry. However, precise, efficient, and rapid bond carboranes that distant from existing functional groups remains intractable owing to limited approaches site-selective control established methods. Herein, we report dative bonding activation strategy nonclassical remote site

Language: Английский

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Recent Developments in Selenylation and Thiolation of Alkenes via Three‐component Reactions

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(14), P. 2310 - 2331

Published: June 24, 2023

Abstract Alkenes are valuable feedstocks in organic synthesis. Selenium or sulfur‐containing coumpounds with a neighboring functional group can be easily prepared by direct difunctionalization of alkenes via three‐component reactions. It will reduce the number steps and waste generation, form complicated molecules from simple starting materials. Herein, recent developments (2013–2022) have been summarized two categories: (1) selenylation seleniranium intermediates Se‐centered radicals; (2) thiolation more diverse mechanisms products Reactions electron‐rich arenes, alcohols, water, acids, NaN 3 , amines, KSCN, sulfamides, TMSNCS, TMSN Et N ⋅ 3HF, SOCl 2 HCl, NFSI, t BuONO, pyridinium salts, BuOOH, ArN BF 4 CO CO, O CF SO Cl, R P(O)−H, (RO) P(O)SH, P(O)OH et al discussed. We hope this review do help for future research area.

Language: Английский

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Strategies and Methods for the Synthesis of 2‐Pyrazolines: Recent Developments (2012–2022)

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(12), P. 1934 - 1969

Published: May 22, 2023

Abstract 2‐Pyrazolines are important five‐membered heterocycles, containing two adjacent nitrogen atoms. They can incorporate various functional groups and possess unique biological properties. Moreover, they have been used as useful building blocks. In recent years, the field of 2‐pyrazoline synthesis has experienced enormous progress. Novel strategies developed, many studies reporting improvements or adaptations existing protocols published, giving access to new functionalizations, unexplored structures, and/or enantioselective synthesis. This review summarizes progress made in synthetic methodologies during period from 2012 2022. The functionalization challenges capabilities, scopes limitations reactions, substitution patterns, mechanisms where appropriate, will be discussed.

Language: Английский

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Nickel-free cross-electrophile coupling of unactivated alkyl bromides with thiosulfonates and sulfinyl sulfones

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(9), P. 2518 - 2527

Published: Jan. 1, 2024

An unusual zinc-promoted reductive coupling between alkyl bromides and thiosulfonates under nickel-free conditions is described.

Language: Английский

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Copper(i)-catalyzed multicomponent interrupted click reaction: modular synthesis of triazole sulfides from elemental sulfur

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(8), P. 1890 - 1896

Published: Jan. 1, 2023

A new multicomponent copper( i )-catalyzed interrupted click reaction which allows the rapid modular synthesis of multisubstituted triazole sulfides including various medium-sized and macrocycles in one-step from elemental sulfur was reported.

Language: Английский

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Catalytic asymmetric synthesis of sulfur-containing atropisomers by C-S bond formations

Science China Chemistry, Journal Year: 2023, Volume and Issue: 66(12), P. 3331 - 3346

Published: Nov. 17, 2023

Language: Английский

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Nickel‐Catalyzed Synthesis of Thioesters from Amides and Disulfides

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(12)

Published: Feb. 8, 2024

Abstract A novel nickel‐catalyzed practical and simple synthesis of thioesters from amides disulfides has been developed. Diverse substituted aromatic are capable coupling with diaryl or dialkyl via C−N/S−S bonds cleavage to produce the desirable in moderate good yields. This procedure features cheap metals, easily preparative substrates, providing a access variety without toxic thiols CO gas.

Language: Английский

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C3 Selective chalcogenation and fluorination of pyridine using classic Zincke imine intermediates

Nature Communications, Journal Year: 2024, Volume and Issue: 15(1)

Published: Aug. 28, 2024

Regioselective C-H functionalization of pyridines remains a persistent challenge due to their inherent electronically deficient properties. In this report, we present strategy for the selective pyridine C3-H thiolation, selenylation, and fluorination under mild conditions via classic N-2,4-dinitrophenyl Zincke imine intermediates. Radical inhibition trapping experiments, as well DFT theoretical calculations, indicated that thiolation selenylation proceeds through radical addition-elimination pathway, whereas two-electron electrophilic substitution pathway. The pre-installed electron-deficient activating N-DNP group plays crucial positive role, with additional benefit recyclability. practicability protocol was demonstrated in gram-scale synthesis late-stage modification pharmaceutically relevant pyridines.

Language: Английский

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