Potassium Carbonate to Unlock a GaCl<sub>3</sub>-Catalyzed C–H Propargylation of Arenes
نویسندگان
چکیده
A gallium-catalyzed C–H propargylation of electron-rich arenes using bromoallenes is described. The development this reaction was first hampered by a side hydroarylation process catalyzed adventitious protons, easily generated from the solvent (1,2-dichloroethane). This hidden Brønsted acid catalysis could be bypassed K2CO3 as an insoluble base. unexpected compatibility base with Lewis catalyst GaCl3 allowed strictly that thoroughly studied kinetics, 71Ga NMR experiments, and DFT computations. GaCl3/K2CO3 system triggers wide range heteroaromatics variety bromoallenes.
منابع مشابه
Lewis acid catalyzed propargylation of arenes with O-propargyl trichloroacetimidates: synthesis of 1,3-diarylpropynes.
The BF3.OEt2-catalyzed Friedel-Crafts propargylation of aromatic compounds with O-propargyl trichloroacetimidates is highly efficient and affords 1,3-diarylpropyne derivatives in good yields.
متن کاملRhenium-catalyzed aromatic propargylation.
A mild aromatic propargylation reaction, employing an air- and moisture-tolerant rhenium-oxo complex ((dppm)ReOCl(3)) as a catalyst and a propargyl alcohol as the electrophile, is described. The reaction tolerates a broad range of functional groups and regioselectively affords propargylic arenas without formation of the isomeric allenyl adducts. The potential of this rhenium(V)-catalyzed reacti...
متن کاملPalladium-Catalyzed Acetylation of Arenes
A simple method for the preparation of aryl methyl ketones is reported. The transformation involves the Pd-catalyzed coupling of an acyl anion equivalent, acetyltrimethylsilane, with aryl bromides to afford the corresponding acetylated arenes in synthetically useful yields. The methodology is tolerant of heterocycles and provides a new method for arene functionalization.
متن کاملIron-catalyzed ene-type propargylation of diarylethylenes with propargyl alcohols.
The diarylalkenyl propargylic complex framework has been found in many natural products and medicinal regents. Herein, we have disclosed an unprecedented FeCl(3) catalyzed ene-type reaction of propargylic alcohols with 1,1-diaryl alkenes which enabled us to furnish a diarylalkenyl propargylic complex framework in moderate to high chemical yields (up to 98%).
متن کاملIodine-catalyzed ammoxidation of methyl arenes.
The development of organic transformation using cheap and readily available substrates under mild conditions will be pivotal for green and sustainable synthetic organic chemistry. Concerning our continued interest in the cyanation reaction, a metal-free direct ammoxidation of readily available methyl arenes leading to nitriles was established under mild conditions. A series of aryl methanes esp...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
ژورنال
عنوان ژورنال: ACS Catalysis
سال: 2021
ISSN: ['2155-5435']
DOI: https://doi.org/10.1021/acscatal.1c03014