{"title":"Cyclization of Vinyl and Aryl Azides into Pyrroles, Indoles, Carbazoles, and Related Fused Pyrroles","authors":"W. F. Berkowitz, S. McCombie","doi":"10.1002/0471264180.OR092.02","DOIUrl":null,"url":null,"abstract":"This chapter reviews in detail those reactions that form of a new pyrrole ring from vinyl, aryl, and heteroaryl azides via formal C–H insertion processes under thermal, photochemical, and metal-catalyzed conditions. These reactions proceed via the intermediacy of vinyl or aryl nitrenes (or their metallonitrene equivalents) and generate a wide variety of pyrroles, indoles, carbazoles, and related systems. Methods for the synthesis of the starting azides are summarized, and a comprehensive survey of the cyclization processes is provided. \n \n \nKeywords: \n \npyrrole; \nindole; \ncarbazole; \nazidoalkene; \nazidoarene; \nvinyl nitrene; \naryl nitrene; \nthermolysis; \nphotolysis; \nmetal catalysis; \nC–H functionalization; \nnitrene; \n2-azidostyrene; \n2-azidobiphenyl","PeriodicalId":19539,"journal":{"name":"Organic Reactions","volume":"34 1","pages":"1-170"},"PeriodicalIF":0.0000,"publicationDate":"2017-06-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"2","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Reactions","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.1002/0471264180.OR092.02","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
引用次数: 2
Abstract
This chapter reviews in detail those reactions that form of a new pyrrole ring from vinyl, aryl, and heteroaryl azides via formal C–H insertion processes under thermal, photochemical, and metal-catalyzed conditions. These reactions proceed via the intermediacy of vinyl or aryl nitrenes (or their metallonitrene equivalents) and generate a wide variety of pyrroles, indoles, carbazoles, and related systems. Methods for the synthesis of the starting azides are summarized, and a comprehensive survey of the cyclization processes is provided.
Keywords:
pyrrole;
indole;
carbazole;
azidoalkene;
azidoarene;
vinyl nitrene;
aryl nitrene;
thermolysis;
photolysis;
metal catalysis;
C–H functionalization;
nitrene;
2-azidostyrene;
2-azidobiphenyl
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