Palladium-Catalyzed Addition of Potassium Aryltrifluoroborates to Aliphatic Nitriles: Synthesis of Alkyl Aryl Ketones, Diketone Compounds, and 2‑Arylbenzo[b]furans

• Published in: Journal of organic chemistry Vol. 78; no. 11; pp. 5273 - 5281
• Main Authors: Wang, Xingyong, Liu, Miaochang, Xu, Long, Wang, Qingzong, Chen, Jiuxi, Ding, Jinchang, Wu, Huayue
• Format: Journal Article
• Language: English
• Published: United States American Chemical Society 07-06-2013
• Subjects: Benzofurans - chemical synthesis; Benzofurans - chemistry; Borates - chemistry; Catalysis; Ketones - chemical synthesis; Ketones - chemistry; Molecular Structure; Nitriles - chemistry; Organometallic Compounds - chemistry; Palladium - chemistry; Potassium - chemistry
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo400433m

A palladium-catalyzed addition of potassium aryltrifluoroborates to aliphatic nitriles has been developed, leading to a wide range of alkyl aryl ketones with moderate to excellent yields. Moreover, several dinitriles (e.g., malononitrile, glutaronitrile, and adiponitrile) were applicable to this process for the construction of 1,3-, 1,5-, or 1,6-dicarbonyl compounds. The scope of the developed approach is successfully explored toward the one-step synthesis of 2-arylbenzo[b]furans via sequential addition and intramolecular annulation reactions. The methodology accepted a wide range of substrates and is applicable to library synthesis.