Minisci-Photoredox-Mediated α-Heteroarylation of N-Protected Secondary Amines: Remarkable Selectivity of Azetidines

Cyril Bosset, Hélène Beucher, Guillaume Bretel, Élisabeth Pasquier, Laurence Quéguiner, Cyril Henry, Ann Vos, James P. Edwards, Lieven Meerpoel, Didier Berthelot

Organic Letters · 2018 · 74 citations · 28 references

Concepts

Abstract

The development of a general, mild, and functional-group-tolerant direct functionalization of N-heteroarenes by C-H functionalization with N-protected amines, including azetidines under Minisci-mediated photoredox conditions, is reported. A broad scope of substituted azetidines, including spirocyclic derivatives, and heterocycles were explored. This reaction enables the production of sp3-rich complex druglike structures in one step from unactivated feedstock amines and heterocycles.

References

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