Lithium bromide/triethylamine promoted tandem cycloaddition–oxidation reaction: A convenient access to 3-trifluoroacetyl pyrroles from N-alkylidene 2-amino esters and β-trifluoroacetyl vinyl ethyl ether

Xin, Yong; Zhao, Jingwei; Han, Jianwei; Zhu, Shizheng

doi:10.1016/j.jfluchem.2010.02.008

Cited by 8 publications

(1 citation statement)

References 16 publications

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“…However, despite considerable progress toward the synthesis of indolizines, there have been very few reports pertaining to the synthesis of pyrroles using a one-pot 1,3-cycloaddition reaction. The few methods that have been reported in this area are generally limited by their requirement for electron-deficient alkyne substrates and their analogues, such as ( E )-1,2-bis(phenylsulfonyl)ethane, ((1-bromovinyl)sulfonyl)benzene, and ( E )-4-ethoxy-1,1,1-trifluorobut-3-en-2-one, which are expensive and difficult to access, as well as lacking in sufficient structural diversity. These limitations could be attributed in part to a lack of suitable methods for the oxidative dehydrogenative aromatization of pyrrolidines.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Pyrrole via a Silver-Catalyzed 1,3-Dipolar Cycloaddition/Oxidative Dehydrogenative Aromatization Tandem Reaction

Liu

Wang

et al. 2017

J. Org. Chem.

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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.

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