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Two‐Step One‐Pot Synthesis of Unsymmetrical (Hetero)Aryl 1,2‐Diketones by Addition‐Oxygenation of Potassium Aryltrifluoroborates to (Hetero)Arylacetonitriles
Author(s) -
Kumar Yogesh,
Jaiswal Yogesh,
Kumar Amit
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201701625
Subject(s) - chemistry , aryl , nucleophile , combinatorial chemistry , catalysis , benzimidazole , quinoxaline , palladium , nucleophilic addition , reaction conditions , organic chemistry , alkyl
An efficient one‐pot two‐step procedure for the synthesis of unsymmetrical (hetero)aryl 1,2‐diketones has been developed. The reaction proceeds through a palladium‐catalyzed nucleophilic addition of potassium aryltrifluoroborates to aliphatic nitriles followed by a copper‐catalyzed aerobic benzylic C–H oxygenation using molecular oxygen as a green oxidant. This represents the first example of the direct synthesis of unsymmetrical diaryl 1,2‐diketones from arylacetonitriles. This method utilizes inexpensive, stable, nontoxic, and readily available starting materials, is highly effective in the presence of both electron‐rich and electron‐poor nitriles and aryltrifluoroborates, and tolerates a wide variety of functional groups. The synthetic utility of this transformation was shown by increasing the scale of the reaction and by carrying out the one‐pot protocol for the preparation of quinoxaline and benzimidazole derivatives. A plausible reaction mechanism has also been proposed.