Benzyne click chemistry

In 2008, Larock and coworkers [54] reported the synthesis of benzotriazoles from benzynes and azides, thus using a so-caUed benzyne click-chemistry approach. The reaction was performed using CsF in acetonitrile it shows wide scope, is rapid, and is conducted under mild conditions (Scheme 9.19). 

Scheme 9.19 The nonmetal catalyzed "benzyne click-chemistry" approach as described by Larock and coworkers [54].

In a recent application of benzyne click chemistry [505], a variety of 1-substituted benzotriazoles (6, R = alkyl, aryl) was prepared by 1,3-dipolar cycloaddition of alkyl or aryl azides to benzyne generated from (2-TMS)phenyltriflate (7) by 1,2-elimination with CsF as fluoride source. This methodology tolerates a wide range of functional groups. 

Shi F, Waldo JP, Chen Y, Larock RC (2008) Benzyne click chemistry synthesis of benzotriazoles from benzynes and azides. Org Lett 10 2409-2412... 

Zhang F, Moses JE (2009) Benzyne click chemistry with in situ generated aromatic azides. Org Lett 11 1587-1590... 

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