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One‐Pot Solvent‐Free Synthesis of Diaryl 1,2‐Diketones by the Sequential Heck Oxidation Reaction of Aryl Halides with Styrenes
Author(s) -
Saberi Dariush,
Hashemi Hajar,
Niknam Khodabakhsh
Publication year - 2017
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201600529
Subject(s) - chemistry , heck reaction , aryl , benzil , reagent , catalysis , organic chemistry , iodide , halide , combinatorial chemistry , alkyl
A novel one‐pot procedure for the synthesis of benzil derivatives was developed by the sequential Heck oxidation reaction of aryl halides (I and Br) with styrenes. In situ‐generated stilbene scaffolds were directly converted to the corresponding diaryl 1,2‐diketones. In the present transformation, tetrabutylammonium iodide (TBAI) was employed as a dual role reagent, one as a reducing agent in Heck reaction and another as a catalyst in the oxidation step. Mechanistic studies showed that molecular oxygen plays a significant part in the oxidation step. Various derivatives of diaryl 1,2‐diketones were synthesized through this protocol in acceptable yields.