Cargando…

Visible Light Photoredox-Catalyzed Decarboxylative Alkylation of 3-Aryl-Oxetanes and Azetidines via Benzylic Tertiary Radicals and Implications of Benzylic Radical Stability

[Image: see text] Four-membered heterocycles offer exciting potential as small polar motifs in medicinal chemistry but require further methods for incorporation. Photoredox catalysis is a powerful method for the mild generation of alkyl radicals for C–C bond formation. The effect of ring strain on r...

Descripción completa

Detalles Bibliográficos
Autores principales:	Dubois, Maryne A. J., Rojas, Juan J., Sterling, Alistair J., Broderick, Hannah C., Smith, Milo A., White, Andrew J. P., Miller, Philip W., Choi, Chulho, Mousseau, James J., Duarte, Fernanda, Bull, James A.
Formato:	Online Artículo Texto
Lenguaje:	English
Publicado:	American Chemical Society 2023
Acceso en línea:	https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10204094/ https://www.ncbi.nlm.nih.gov/pubmed/36868184 http://dx.doi.org/10.1021/acs.joc.3c00083

Ejemplares similares

Lithium‐Catalyzed Thiol Alkylation with Tertiary and Secondary Alcohols: Synthesis of 3‐Sulfanyl‐Oxetanes as Bioisosteres
por: Croft, Rosemary A., et al.
Publicado: (2017)

Oxetan-3-ols as 1,2-bis-Electrophiles in a Brønsted-Acid-Catalyzed Synthesis of 1,4-Dioxanes
por: Rojas, Juan J., et al.
Publicado: (2022)

Structurally Divergent Lithium Catalyzed Friedel–Crafts Reactions on Oxetan‐3‐ols: Synthesis of 3,3‐Diaryloxetanes and 2,3‐Dihydrobenzofurans
por: Croft, Rosemary A., et al.
Publicado: (2016)

Synthesis of New Azetidine and Oxetane Amino Acid Derivatives through Aza-Michael Addition of NH-Heterocycles with Methyl 2-(Azetidin- or Oxetan-3-Ylidene)Acetates
por: Gudelis, Emilis, et al.
Publicado: (2023)

Metal-free direct alkylation of unfunctionalized allylic/benzylic sp(3) C–H bonds via photoredox induced radical cation deprotonation
por: Zhou, Rong, et al.
Publicado: (2017)

A dual photoredox-nickel strategy for remote functionalization via iminyl radicals: radical ring-opening-arylation, -vinylation and -alkylation cascades
por: Dauncey, Elizabeth M., et al.
Publicado: (2019)

Correction: A dual photoredox-nickel strategy for remote functionalization via iminyl radicals: radical ring-opening-arylation, -vinylation and -alkylation cascades
por: Dauncey, Elizabeth M., et al.
Publicado: (2019)

Hydrogen radical-shuttle (HRS)-enabled photoredox synthesis of indanones via decarboxylative annulation
por: Yang, Bo, et al.
Publicado: (2021)

Oxetanes in Drug Discovery Campaigns
por: Rojas, Juan J., et al.
Publicado: (2023)

O-Benzyl Xanthate Esters under Ni/Photoredox Dual Catalysis: Selective Radical Generation and Csp(3)–Csp(2) Cross-Coupling
por: Vara, Brandon A., et al.
Publicado: (2017)

Visible-Light Photoredox-Catalyzed Amidation of Benzylic Alcohols
por: Gaspa, Silvia, et al.
Publicado: (2020)

Phosphoranyl Radical Fragmentation Reactions Driven by Photoredox Catalysis
por: Rossi-Ashton, James A., et al.
Publicado: (2020)

Enantioselective benzylic C–H arylation via photoredox and nickel dual catalysis
por: Cheng, Xiaokai, et al.
Publicado: (2019)

Formal enantioconvergent substitution of alkyl halides via catalytic asymmetric photoredox radical coupling
por: Li, Jiangtao, et al.
Publicado: (2018)

Investigating the Mechanism of Ni-Catalyzed Coupling of Photoredox-Generated Alkyl Radicals and Aryl Bromides: A Computational Study
por: Sanosa, Nil, et al.
Publicado: (2023)

Bioinspired Cobalt-Catalysis Enables Generation of Nucleophilic Radicals from Oxetanes
por: Potrząsaj, Aleksandra, et al.
Publicado: (2022)

Photoredox-catalyzed stereoselective alkylation of enamides with N-hydroxyphthalimide esters via decarboxylative cross-coupling reactions
por: Guo, Jing-Yu, et al.
Publicado: (2019)

Benzylic C−H acylation by cooperative NHC and photoredox catalysis
por: Meng, Qing-Yuan, et al.
Publicado: (2021)

1,4-Dihydropyridines as Alkyl Radical Precursors: Introducing the Aldehyde Feedstock to Nickel/Photoredox Dual Catalysis
por: Gutiérrez-Bonet, Álvaro, et al.
Publicado: (2016)

Photoredox catalysis enabling decarboxylative radical cyclization of γ,γ-dimethylallyltryptophan (DMAT) derivatives: formal synthesis of 6,7-secoagroclavine
por: Regni, Alessio, et al.
Publicado: (2023)

Photoredox Cross-Coupling: Ir/Ni Dual Catalysis for the Synthesis of Benzylic Ethers
por: Karakaya, Idris, et al.
Publicado: (2015)

Hypervalent iodine(III)-mediated decarboxylative acetoxylation at tertiary and benzylic carbon centers
por: Kiyokawa, Kensuke, et al.
Publicado: (2018)

Radical Decarboxylative Carbon–Nitrogen Bond Formation
por: Li, Xiangting, et al.
Publicado: (2023)

Selective electrochemical generation of benzylic radicals enabled by ferrocene-based electron-transfer mediators
por: Lennox, Alastair J. J., et al.
Publicado: (2017)

Gram-Scale Synthesis of Flavoring Ketones in One Pot via Alkylation–Decarboxylation on Benzylic Carbon Using a Commercial Solid Acid Catalyst
por: Naikwadi, Dhanaji R., et al.
Publicado: (2020)

Rhodium-catalyzed direct alkylation of benzylic amines using alkyl bromides
por: Anschuber, Martin, et al.
Publicado: (2018)

Arylboronic Acid Catalyzed C-Alkylation and Allylation Reactions Using Benzylic Alcohols
por: Estopiñá-Durán, Susana, et al.
Publicado: (2020)

Radical condensation between benzylic alcohols and acetamides to form 3-arylpropanamides
por: Azizi, Kobra, et al.
Publicado: (2020)

Mild, visible light-mediated decarboxylation of aryl carboxylic acids to access aryl radicals
por: Candish, L., et al.
Publicado: (2017)

Allylic C(sp(3))–H alkylation via synergistic organo- and photoredox catalyzed radical addition to imines
por: Jia, Jiaqi, et al.
Publicado: (2020)

Investigating 3,3-diaryloxetanes as potential bioisosteres through matched molecular pair analysis
por: Dubois, Maryne A. J., et al.
Publicado: (2021)

Photoredox-Mediated Routes to Radicals: The Value of Catalytic Radical Generation in Synthetic Methods Development
por: Matsui, Jennifer K., et al.
Publicado: (2017)

Visible-light mediated catalytic asymmetric radical deuteration at non-benzylic positions
por: Shi, Qinglong, et al.
Publicado: (2022)

Methyl Substitution Destabilizes Alkyl Radicals
por: Blokker, Eva, et al.
Publicado: (2022)

Copper-catalysed benzylic C–H coupling with alcohols via radical relay enabled by redox buffering
por: Hu, Huayou, et al.
Publicado: (2020)

Nickel-Catalyzed Stereoselective Coupling Reactions of Benzylic and Alkyl Alcohol Derivatives
por: Herbert, Claire A., et al.
Publicado: (2023)

Investigations of alkynylbenziodoxole derivatives for radical alkynylations in photoredox catalysis
por: Pan, Yue, et al.
Publicado: (2018)

Metal‐Free Radical Borylation of Alkyl and Aryl Iodides
por: Cheng, Ying, et al.
Publicado: (2018)

Photocatalytic deaminative benzylation and alkylation of tetrahydroisoquinolines with N-alkylpyrydinium salts
por: Schönbauer, David, et al.
Publicado: (2020)

Using the Colloidal Method to Prepare Au Catalysts for the Alkylation of Aniline by Benzyl Alcohol
por: Hare, Luka V., et al.
Publicado: (2023)

Cannot write session to /tmp/vufind_sessions/sess_194eq19dmvn3u0bppn3aqvqthp