Jiangsu Key Laboratory for Chemistry of Low-Dimensional Materials, School of Chemistry and Chemical Engineering, Huaiyin Normal University , Huaian 223300, P. R. China.
School of Material Science and Engineering, Southwest University of Science and Technology , Mianyang 621010, P. R. China.
J Org Chem. 2017 Apr 21;82(8):4194-4202. doi: 10.1021/acs.joc.7b00180. Epub 2017 Apr 5.
Pyrroles are an important group of heterocyclic compounds with a wide range of interesting properties, which have resulted in numerous applications in a variety of fields. Despite the importance of these compounds, there have been few reports in the literature pertaining to the synthesis of pyrroles from simple alkenes using a one-pot sequential 1,3-dipolar cycloaddition/aromatization reaction sequence. Herein, we report the development of a benzoyl peroxide-mediated oxidative dehydrogenative aromatization reaction for the construction of pyrroles. We subsequently developed a one-pot tandem reaction that combined this new method with a well-defined silver-catalyzed 1,3-dipolar cycloaddition reaction, thereby providing a practical method for the synthesis of multisubstituted pyrroles from easy available alkenes. The mechanism of this oxidative dehydrogenative aromatization reaction was also examined in detail.
吡咯是一类具有广泛有趣性质的重要杂环化合物，在许多领域都有许多应用。尽管这些化合物很重要，但文献中很少有报道涉及使用一锅顺序 1,3-偶极环加成/芳构化反应序列从简单烯烃合成吡咯。在这里，我们报告了过氧化苯甲酰介导的氧化脱氢芳构化反应用于构建吡咯。随后，我们开发了一种一锅串联反应，将这种新方法与银催化的 1,3-偶极环加成反应相结合，从而为从易得的烯烃合成多取代吡咯提供了一种实用的方法。还详细研究了这种氧化脱氢芳构化反应的机理。
