Mild and selective base-free C–H arylation of heteroarenes: experiment and computation† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c6sc02595a Click here for additional data file.
نویسندگان
چکیده
Amild and selective C–H arylation strategy for indoles, benzofurans and benzothiophenes is described. The arylation method engages aryldiazonium salts as arylating reagents in equimolar amounts. The protocol is operationally simple, base free, moisture tolerant and air tolerant. It utilizes low palladium loadings (0.5 to 2.0 mol% Pd), short reaction times, green solvents (EtOAc/2-MeTHF or MeOH) and is carried out at room temperature, providing a broad substrate scope (47 examples) and excellent selectivity (C-2 arylation for indoles and benzofurans, C-3 arylation for benzothiophenes). Mechanistic experiments and DFT calculations support a Heck–Matsuda type coupling mechanism.
منابع مشابه
C–H arylation of triphenylene, naphthalene and related arenes using Pd/C† †Electronic supplementary information (ESI) available. CCDC 1013416 and 1013417. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c4sc03051f Click here for additional data file. Click here for additional data file.
متن کامل
Stoichiometric to catalytic reactivity of the aryl cycloaurated species with arylboronic acids: insight into the mechanism of gold-catalyzed oxidative C(sp2)–H arylation† †Electronic supplementary information (ESI) available: Detailed experimental procedures, analytical data. CCDC 1000469, 1007212 and 1019879. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c4sc02070g Click here for additional data file. Click here for additional data file.
متن کامل
A new face of phenalenyl-based radicals in the transition metal-free C–H arylation of heteroarenes at room temperature: trapping the radical initiator via C–C σ-bond formation† †Electronic supplementary information (ESI) available. CCDC 1520738. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c7sc02661g Click here for additional data file. Click here for additional data file.
The radical-mediated transition metal-free approach for the direct C–H bond functionalization of arenes is considered as a cost effective alternative to transition metal-based catalysis. An organic ligand-based radical plays a key role by generating an aryl radical which undergoes a subsequent functionalization process. The design principle of the present study takes advantage of a relatively s...
متن کاملPhotoredox-mediated Minisci C–H alkylation of N-heteroarenes using boronic acids and hypervalent iodine† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c6sc02653b Click here for additional data file.
A photoredox-mediated Minisci C–H alkylation reaction of N-heteroarenes with alkyl boronic acids is reported. A broad range of primary and secondary alkyl groups can be efficiently incorporated into various N-heteroarenes using [Ru(bpy)3]Cl2 as photocatalyst and acetoxybenziodoxole as oxidant under mild conditions. The reaction exhibits excellent substrate scope and functional group tolerance, ...
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عنوان ژورنال:
دوره 8 شماره
صفحات -
تاریخ انتشار 2017