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Coordinating activation strategy for C(sp3)–H/C(sp3)–H cross-coupling to access β-aromatic α-amino acids
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Coordinating activation strategy for C(sp3)–H/C(sp3)–H cross-coupling to access β-aromatic α-amino acids
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Journal Article
Coordinating activation strategy for C(sp3)–H/C(sp3)–H cross-coupling to access β-aromatic α-amino acids
2015
Overview
The past decade has witnessed significant advances in C–H bond functionalizations with the discovery of new mechanisms. Non-precious transition-metal-catalysed radical oxidative coupling for C(
sp
3
)–H bond transformations is an appealing strategy for C–C bond formations. The radical oxidative C(
sp
3
)–H/C(
sp
3
)–H cross-coupling reactions of α-C(
sp
3
)–H bonds of amines with free radicals represent a conceptual and practical challenge. We herein develop the coordinating activation strategy to illustrate the nickel-catalysed radical oxidative cross-coupling between C(
sp
3
)–H bonds and (hetero)arylmethyl free radicals. The protocol can tolerate a rich variety of α-amino acids and (hetero)arylmethanes as well as arylmethylenes and arylmethines, affording a large library of α-tertiary and α-quaternary β-aromatic α-amino acids. This process also features low-cost metal catalyst, readily handled and easily removable coordinating group, synthetic simplicity and gram-scale production, which would enable the potential for economical production at commercial scale in the future.
Oxidative coupling of two C(sp3)-H groups is an attractive approach for the formation of carbon-carbon bonds, building structural complexity while avoiding the formation of waste salts. Here, the authors report such a transformation, using a nickel catalyst to functionalise amino acids with benzylic radicals.
Publisher
Nature Publishing Group UK,Nature Pub. Group
