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Silver(I)-mediated Reaction of 2-Isocyanobiaryl with Alkyl Trifluoroborates: Efficient Synthesis of 6-Alkylated Phenanthridines

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A silver-mediated free-radical cascade cyclization of isocyanides with potassium alkyl trifluoroborates was developed. The procedure tolerates a series of functional groups, including chloro, bromo, ester, ketone, and amide. Additionally, it… Click to show full abstract

A silver-mediated free-radical cascade cyclization of isocyanides with potassium alkyl trifluoroborates was developed. The procedure tolerates a series of functional groups, including chloro, bromo, ester, ketone, and amide. Additionally, it is not sensitive to steric hindrance. Thus, this reaction represents a very useful strategy for the production of 6-alkylated phenanthridine derivatives. The addition of alkyl radical to the isonitrile, followed by a radical aromatic cyclization, is involved in this transformation.

Keywords: reaction isocyanobiaryl; alkyl trifluoroborates; silver mediated; mediated reaction

Journal Title: Chemistry Letters
Year Published: 2018

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