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Cobalt-catalysed site-selective intra- and intermolecular dehydrogenative amination of unactivated sp3 carbons
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Cobalt-catalysed site-selective intra- and intermolecular dehydrogenative amination of unactivated sp3 carbons
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Journal Article
Cobalt-catalysed site-selective intra- and intermolecular dehydrogenative amination of unactivated sp3 carbons
2015
Overview
Cobalt-catalysed sp
2
C–H bond functionalization has attracted considerable attention in recent years because of the low cost of cobalt complexes and interesting modes of action in the process. In comparison, much less efforts have been devoted to the sp
3
carbons. Here we report the cobalt-catalysed site-selective dehydrogenative cyclization of aliphatic amides via a C–H bond functionalization process on unactivated sp
3
carbons with the assistance of a bidentate directing group. This method provides a straightforward synthesis of monocyclic and spiro β- or γ-lactams with good to excellent stereoselectivity and functional group tolerance. In addition, a new procedure has been developed to selectively remove the directing group, which enables the synthesis of free β- or γ-lactam compounds. Furthermore, the first cobalt-catalysed intermolecular dehydrogenative amination of unactivated sp
3
carbons is also realized.
Functionalizing unactivated carbon–hydrogen bonds is challenging, especially when using non-precious metals and dealing with sp
3
hybridized carbons. Here, the authors report an intramolecular cobalt catalysed amination of C–H bonds of sp
3
carbons, giving access to β- and γ-lactams.
Publisher
Nature Publishing Group UK,Nature Publishing Group,Nature Pub. Group
