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In 2014, Yu and coworkers reported the first meta‐selective C–H acetoxylation of benzylamine derivatives using the template that previously worked for anilines (Scheme 2.24) [31]. The versatility of the reaction was demonstrated with both acyclic and cyclic benzylamines, although only a few examples were investigated. Notably, since 2‐phenylpyrrolidine and 2‐phenylpiperidine motifs are often found in medicinally important heterocycles, this meta‐selective C–H acetoxylation method is a potentially powerful methodology for accessing diverse structures of medicinally importance.

Scheme 2.24 meta‐C–H acetoxylation of benzylamine derivatives.

Source: Modified from Tang et al. [31].

Besides meta‐C–H acetoxylation of benzylamines, meta‐C–H olefination was also reported by Xu, Xu, Jin, and coworkers through a quaternary ammonium salt assembly of the template for tertiary benzylamines [33]. Remarkably, this method was demonstrated to be applicable to several distal arene‐tethered tertiary amine derivatives, although only a few examples of benzylamine derivatives were tested (Scheme 2.25).

Scheme 2.25 meta‐C–H olefination of tertiary benzylamines and distal arene‐tethered tertiary amine derivatives.