Benzo[b]azepines are important structural motifs for the pharmaceutical industry. However, their syntheses are usually lengthy, involving several steps, transition-metal catalysts, and/or harsh conditions. A novel, general, mild, and metal-free oxidative ring expansion tandem reaction of hydroquinolines with TMSCHN 2 as a versatile soft nucleophile to gain access to these valuable compounds in a simple and straightforward manner is presented.
A simple and mild
Cu-catalyzed oxidative three-component oxidative
Ugi-type method for the synthesis of a variety of substituted imides
has been developed. In this direct imidation approach, benzoyl peroxide
serves as both the oxidant and the carboxylate source, allowing not
only the functionalization of C(sp3)–H bonds in
α-position to an amine but also benzylic substrates. This procedure
presents a wide substrate-type and functional group tolerance. Moreover,
the mildness of the method permitted us to extend its application
to the late stage functionalization of complex natural products such
as the alkaloids brucine and strychnine, leading to interesting highly
functionalized imide derivatives. On the basis of experimental and
computational studies, a plausible mechanism has been proposed.
In this highlight, the design of cooperative non-covalent organocatalysis for the development of novel asymmetric oxidative C–H bond functionalization reactions is presented.
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