[3 + 2] cycloaddition and subsequent oxidative dehydrogenation between alkenes and diazo compounds: a simple and direct approach to pyrazoles using TBAI/TBHP. Issue 36 (19th August 2016)

• Record Type: Journal Article
• Authors: Shao, Ying; Tong, Jingjing; Zhao, Yanwei; Zheng, Hao; Ma, Liang; Ma, Meihua; Wan, Xiaobing
• Is Part Of: Organic & biomolecular chemistry. Volume 14:Issue 36(2016)
• Page Start: 8486
• Page End: 8492
• Publication Date: 2016-08-19
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c6ob01522k
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : Herein, an efficient [3 + 2] cycloaddition and oxidative dehydrogenation reaction of diazo compounds and alkenes was well developed using TBAI/TBHP, leading to pyrazoles with moderate to high yields. Abstract : A novel Bu4 NI-catalyzed pyrazole formation reaction is well described via sequential [3 + 2] cycloaddition and oxidative dehydrogenation reactions using TBHP as the primary oxidant. In comparison with previous cases toward pyrazoles from alkenes and diazo compounds, alkenes without a pre-organized leaving group were applied in this transformation. In addition, this methodology was distinguished by its broad substrate scope, commercially available inexpensive starting materials, high atom economy and operational simplicity.