Coordinating activation strategy for C(sp3)–H/C(sp3)–H cross-coupling to access β-aromatic α-amino acids

Kaizhi Li, Qian Wu, Jingbo Lan and Jingsong You ()
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Kaizhi Li: Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, and State Key Laboratory of Biotherapy, West China Hospital, West China Medical School, Sichuan University
Qian Wu: Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, and State Key Laboratory of Biotherapy, West China Hospital, West China Medical School, Sichuan University
Jingbo Lan: Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, and State Key Laboratory of Biotherapy, West China Hospital, West China Medical School, Sichuan University
Jingsong You: Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, and State Key Laboratory of Biotherapy, West China Hospital, West China Medical School, Sichuan University

Nature Communications, 2015, vol. 6, issue 1, 1-9

Abstract: Abstract 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(sp3)–H bond transformations is an appealing strategy for C–C bond formations. The radical oxidative C(sp3)–H/C(sp3)–H cross-coupling reactions of α-C(sp3)–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(sp3)–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.

Date: 2015
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DOI: 10.1038/ncomms9404

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