3 years ago

Renaissance of Sandmeyer-Type Reactions: Conversion of Aromatic C–N Bonds into C–X Bonds (X = B, Sn, P, or CF3)

Renaissance of Sandmeyer-Type Reactions: Conversion
of Aromatic C–N Bonds into C–X Bonds (X = B, Sn, P,
or CF3)
Di Qiu, Yan Zhang, Jianbo Wang, Fanyang Mo
The Sandmeyer reaction represents an important organic transformation that converts an arylamine to an aryl halide using Cu(I) halide via a diazonium salt intermediate. The reaction was first reported by Sandmeyer in 1884, and a number of named reactions closely related to it have been developed and widely applied in organic synthesis throughout the 20th century. These include the Pschorr reaction for the synthesis of biaryl tricycles, the Gomberg–Bachmann reaction for biaryl formations, the Balz–Schiemann reaction for C–F bond formations, and the Meerwein reaction for arylation of α,β-unsaturated carbonyl compounds. However, all these reactions were discovered before 1940. In 1977, Doyle and co-workers reported an organic phase diazotization process, and Kikukawa and Matsuda used aryldiazonium salts in transition metal-catalyzed cross-coupling reactions. However, completely new processes involving diazonium salts have been seldom reported since then, although aryldiazonium salts are widely utilized in modern organic synthesis.

Publisher URL: http://dx.doi.org/10.1021/acs.accounts.7b00566

DOI: 10.1021/acs.accounts.7b00566

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