The synthesis of O/S-heterocycles starting from β-nitrostyrenes: A recent update

Tetrahedron, Journal Year: 2023, Volume and Issue: 149, P. 133717 - 133717

Published: Nov. 2, 2023

Language: Английский

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Electrochemical Cascade Cyclization of N‐Centered Radicals with Electro‐Deficient Alkynes

ChemCatChem, Journal Year: 2024, Volume and Issue: 16(8)

Published: Jan. 25, 2024

Abstract Indoline‐fused polycyclic scaffolds are virtually universal in biological and pharmaceutical. Here we demonstrate a facile electrooxidative cascade cyclization for indoline‐based derivatives, employing amidyl radicals with ynones under mild conditions. The efficient method enables the formation of two new C−N C−C bonds single step high regioselectivity. Various tetracyclic 6/5/6/6 skeletons can be achieved through biscyclization/dehydrogenation process. Additionally, this electrochemical strategy proceeds sustainable metal‐ oxidant‐free condition, H 2 being solely byproduct.

Language: Английский

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Visible‐Light Promoted Minisci–Type Cyanoalkylation of Azauracils via C−C Bond Cleavage

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(22)

Published: March 16, 2024

Abstract A photo‐induced Minisci–type cyanoalkylation of azauracils was developed under metal‐free and base‐free conditions. Readily available cyclobutanone oxime esters were used as the cyanoalkylating reagents via C−C bond cleavage to generate γ‐cyanoalkyl azauracil derivatives in good moderate yields. The introduced cyano group can be easily converted into many other functional groups, thus makes current protocol more practical.

Language: Английский

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Catalytic Contra-Thermodynamic Isomerization–Asymmetric Hydroboration of Alkenyl Alcohols and Amines

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(7), P. 5458 - 5468

Published: March 28, 2024

Catalytic isomerization of alkenes is a powerful tool for the construction complex synthetically valuable molecules due to their redox-neutral, atom- and step-economical nature. However, traditional catalytic asymmetric typically required use heteroatomic group such as OH or NR2 thermodynamic driving force (i.e., C═C double bond isomerizes along direction groups). Here, we present contra-thermodynamic isomerization/asymmetric hydroboration alkenyl alcohols amines, in which opposite OR NR2. Compared thermal isomerizations, this reaction overcomes unfavorable bias form alkene intermediate, followed by an irreversible terminal provide highly chiral 1,n-boryl ethers amines. This protocol shows wide substrate scope, including allylic alcohols, homoallylic protected various free The synthetic utilities practicability method were demonstrated gram-scale reactions, diverse product transformations, its applications synthesis bioactive molecules. Preliminary mechanistic studies show that involves dissociative 1,1-disubstituted intermediates.

Language: Английский

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Iron-catalyzed reductive cyclization of nitroarenes: Synthesis of aza-heterocycles and DFT calculations

Chinese Chemical Letters, Journal Year: 2022, Volume and Issue: 34(3), P. 107758 - 107758

Published: Aug. 18, 2022

Language: Английский

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Recent Advances in Molecule Synthesis Involving C-C Bond Cleavage of Ketoxime Esters

Molecules, Journal Year: 2023, Volume and Issue: 28(6), P. 2667 - 2667

Published: March 15, 2023

The synthetic strategies of oxime derivatives participating in radical-type reactions have been rapidly developed the last few decades. Among them, N–O bond cleavage esters leading to formation nitrogen-centered radicals triggers adjacent C–C produce carbon-centered free radicals, which has virtually used organic synthesis recent years. Herein, we summarized radical involving and through this special reaction form, including those from acyl ester cyclic ketoxime derivatives. These contents were systematically classified according different types. In review, after 2021 included, with emphasis on substrate scope mechanism.

Language: Английский

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Copper-catalyzed [1,3]-nitrogen rearrangement ofO-aryl ketoximesviaoxidative addition of N–O bond in inverse electron flow

Chemical Science, Journal Year: 2023, Volume and Issue: 14(21), P. 5705 - 5711

Published: Jan. 1, 2023

[1,3]-Nitrogen rearrangement reactions of O -aryl ketoximes was catalytically promoted by IPrCuBr and BF 3 ·OEt 2 . The oxidative addition the N–O bond to Cu catalyst is accelerated donation electrons from both nitrogen oxygen atoms.

Language: Английский

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[4 + 3] Cycloaddition of ketenimines with furocarbenoids: Divergent and efficient synthesis of fused cycloheptatriene and tropone scaffolds

Chinese Chemical Letters, Journal Year: 2022, Volume and Issue: 34(5), P. 107823 - 107823

Published: Sept. 15, 2022

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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Synthesis of multisubstituted carbazol-4-amines from tetrahydrocarbazol-4-one oximes

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(10), P. 2821 - 2828

Published: Jan. 1, 2024

A sequential synthetic method toward 1,3-disubstituted carbazol-4-amines is reported and an interesting C–S metathesis process disclosed.

Language: Английский

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