Non-Directed, Copper Catalyzed Benzylic C-H Amination Avoiding Substrate Excess

15 July 2019, Version 3
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

We report the development of a benzylic C-H amination protocol that addresses two common drawbacks in non-directed, intermolecular benzylic C-H aminations: (i) the need to use an excess of substrate and (ii) the limitation to only introduce one type of nitrogen source. Key to this discovery is the use of the strong oxidant N-fluorobenzenesulfonimide (NFSI) in combination with a Cu/diimine ligand catalyst system and an added nitrogen nucleophile. The established conditions allow to lower the C-H substrate loading to 1.0 equivalent and provide up to 95% yield of C-H amination product. Furthermore, sulfonamides and benzamides can be employed as nitrogen sources/nucleophiles, resulting in access to a diverse product scope.

Keywords

C-H amination
earth-abundant base metal catalyst
copper
C-H Functionalization
catalysis chemistry
Synthesis
benzylic amine moiety
Intermolecular Couplings
diimine ligand
NFSI

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