Cargando…

Mechanistic analysis of a copper-catalyzed C–H oxidative cyclization of carboxylic acids

We recently reported that carboxylic acids can be oxidized to lactone products by potassium persulfate and catalytic copper acetate. Here, we unravel the mechanism for this C–H functionalization reaction using desorption electrospray ionization, online electrospray ionization, and tandem mass spectr...

Descripción completa

Detalles Bibliográficos
Autores principales:	Banerjee, Shibdas, Sathyamoorthi, Shyam, Du Bois, J., Zare, Richard N.
Formato:	Online Artículo Texto
Lenguaje:	English
Publicado:	Royal Society of Chemistry 2017
Materias:	Chemistry
Acceso en línea:	https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5642147/ https://www.ncbi.nlm.nih.gov/pubmed/29147527 http://dx.doi.org/10.1039/c7sc02240a

Ejemplares similares

Site-selective bromination of sp(3) C–H bonds
por: Sathyamoorthi, Shyam, et al.
Publicado: (2017)

Copper-catalyzed asymmetric cyclization of alkenyl diynes: method development and new mechanistic insights
por: Zhu, Xin-Qi, et al.
Publicado: (2021)

Salient features of the aza-Wacker cyclization reaction
por: Thomas, Annu Anna, et al.
Publicado: (2020)

An improved synthesis of telmisartan via the copper-catalyzed cyclization of o-haloarylamidines
por: Zhang, Junchi, et al.
Publicado: (2020)

Palladium-catalyzed dehydrogenative C–H cyclization for isoindolinone synthesis
por: Abe, Masahiro, et al.
Publicado: (2021)

Facile synthesis of isoquinolines and isoquinoline N-oxides via a copper-catalyzed intramolecular cyclization in water
por: Zhang, Lujun, et al.
Publicado: (2022)

Copper-catalyzed enantioselective diyne cyclization via C(sp(2))–O bond cleavage
por: Zhou, Ji-Jia, et al.
Publicado: (2023)

Mechanistic insights into copper-catalyzed aerobic oxidative coupling of N–N bonds
por: Ryan, Michael C., et al.
Publicado: (2019)

Rh-catalyzed aerobic oxidative cyclization of anilines, alkynes, and CO
por: Li, Xinyao, et al.
Publicado: (2017)

Copper-Catalyzed Dimerization/Cyclization of Itaconates
por: Li, Zhiqiang, et al.
Publicado: (2015)

Mechanistic study of the rhodium-catalyzed carboxylation of simple aromatic compounds with carbon dioxide
por: Suga, Takuya, et al.
Publicado: (2017)

Copper-Catalyzed Dual Cyclization for the Synthesis of Quinindolines
por: Wang, Hung-Kai, et al.
Publicado: (2020)

Copper-catalyzed C–H acyloxylation of 2-phenylpyridine using oxygen as the oxidant
por: Wang, Feifan, et al.
Publicado: (2018)

Rh(iii)-catalyzed diastereoselective C–H bond addition/cyclization cascade of enone tethered aldehydes
por: Boerth, Jeffrey A., et al.
Publicado: (2016)

Enantioselective Nazarov cyclization of indole enones cooperatively catalyzed by Lewis acids and chiral Brønsted acids
por: Wang, Guo-Peng, et al.
Publicado: (2017)

Enantioselective Copper‐Catalyzed Borylative Cyclization for the Synthesis of Quinazolinones
por: Dherbassy, Quentin, et al.
Publicado: (2021)

Copper-catalyzed stereo- and regioselective hydrophosphorylation of terminal alkynes: scope and mechanistic study
por: Li, Junchen, et al.
Publicado: (2022)

Cascade aza-Michael Addition-Cyclizations; Toward Renewable and Multifunctional Carboxylic Acids for Melt-Polycondensation
por: Noordzij, Geert J., et al.
Publicado: (2019)

Nickel-catalyzed cyclization of alkyne-nitriles with organoboronic acids involving anti-carbometalation of alkynes
por: Zhang, Xingjie, et al.
Publicado: (2016)

Progress and prospects in copper-catalyzed C–H functionalization
por: Aneeja, Thaipparambil, et al.
Publicado: (2020)

Copper-Catalyzed Decarboxylative Elimination of Carboxylic Acids to Styrenes
por: Stanton, Michael P., et al.
Publicado: (2023)

Facile synthesis of 2-substituted benzo[b]furans and indoles by copper-catalyzed intramolecular cyclization of 2-alkynyl phenols and tosylanilines
por: Rong, Zhouting, et al.
Publicado: (2019)

Cobalt-catalyzed enantioselective desymmetrizing reductive cyclization of alkynyl cyclodiketones
por: Liang, Ren-Xiao, et al.
Publicado: (2023)

Copper-catalyzed oxidative benzylic C-H cyclization via iminyl radical from intermolecular anion-radical redox relay
por: Shan, Xiang-Huan, et al.
Publicado: (2019)

Mechanistic insights into cobalt(ii/iii)-catalyzed C–H oxidation: a combined theoretical and experimental study
por: Guo, Xiao-Kang, et al.
Publicado: (2015)

Preparative microdroplet synthesis of carboxylic acids from aerobic oxidation of aldehydes
por: Yan, Xin, et al.
Publicado: (2018)

Copper-catalyzed propargylic C–H functionalization for allene syntheses
por: Zhang, Dongjie, et al.
Publicado: (2023)

Rhodium catalyzed cascade cyclization featuring B–H and C–H activation: one-step construction of carborane-fused N-polyheterocycles
por: Lyu, Hairong, et al.
Publicado: (2018)

Understanding the unique reactivity patterns of nickel/JoSPOphos manifold in the nickel-catalyzed enantioselective C–H cyclization of imidazoles
por: Liu, Jian-Biao, et al.
Publicado: (2020)

A copper-catalyzed four-component reaction of arylcyclopropanes, nitriles, carboxylic acids and N-fluorobenzenesulfonimide: facile synthesis of imide derivatives
por: Yang, Shengbiao, et al.
Publicado: (2022)

Divergent synthesis of flavones and flavanones from 2′-hydroxydihydrochalcones via palladium(ii)-catalyzed oxidative cyclization
por: Son, Seung Hwan, et al.
Publicado: (2021)

Copper(ii)-catalyzed tandem cyclization for the synthesis of benzo[d][1,3]thiazin-2-yl phosphonates involving C–P and C–S bond formation
por: Liu, Yang, et al.
Publicado: (2020)

Copper-catalyzed [3 + 1] cyclization of cyclopropenes/diazo compounds and bromodifluoroacetamides: facile synthesis of α,α-difluoro-β-lactam derivatives
por: Zhang, Mengru, et al.
Publicado: (2021)

Mechanistic analysis of an asymmetric palladium-catalyzed conjugate addition of arylboronic acids to β-substituted cyclic enones
por: Boeser, Cornelia L., et al.
Publicado: (2015)

A facile method for Rh-catalyzed decarbonylative ortho-C–H alkylation of (hetero)arenes with alkyl carboxylic acids
por: Tian, Yiqiang, et al.
Publicado: (2021)

Facile synthesis of axially chiral styrene-type carboxylic acids via palladium-catalyzed asymmetric C–H activation
por: Yang, Chi, et al.
Publicado: (2021)

Comparative DFT study of metal-free Lewis acid-catalyzed C–H and N–H silylation of (hetero)arenes: mechanistic studies and expansion of catalyst and substrate scope
por: Du, Pan, et al.
Publicado: (2019)

DMSO-mediated palladium-catalyzed cyclization of two isothiocyanates via C–H sulfurization: a new route to 2-aminobenzothiazoles
por: Yao, Guangkai, et al.
Publicado: (2019)

Practical scale up synthesis of carboxylic acids and their bioisosteres 5-substituted-1H-tetrazoles catalyzed by a graphene oxide-based solid acid carbocatalyst
por: Mittal, Rupali, et al.
Publicado: (2021)

Phosphine Oxide-Promoted Rh(I)-Catalyzed C–H Cyclization of Benzimidazoles with Alkenes
por: Lu, Mingzhen, et al.
Publicado: (2023)

Cannot write session to /tmp/vufind_sessions/sess_bfkrqf9g8e68is8bnj8v4p8n6r