6-Phosphorylated Phenanthridines from 2-Isocyanobiphenyls via Radical C–P and C–C Bond Formation

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• 作者：Bo Zhang ; Constantin Gabriel Daniliuc ; Armido Studer
• 刊名：Organic Letters
• 出版年：2014
• 出版时间：January 3, 2014
• 年：2014
• 卷：16
• 期：1
• 页码：250-253
• 全文大小：284K
• ISSN：1523-7052

文摘

A C鈥揚 bond and a C鈥揅 bond are formed in the synthesis of 6-phosphorylated phenanthridines starting with readily prepared 2-isocyanobiphenyls and commercially available P-radical precursors. The radical cascade reaction comprises addition of an oxidatively generated P-centered radical to the isonitrile functionality and subsequent homolytic aromatic substitution. Various 6-phosphorylated phenanthridines are formed in moderate to excellent yield. In contrast to the currently intensively investigated direct arene phosphorylation, the arene core is constructed with concomitant phosphorylation using this approach.