Abstract
A ruthenium-catalyzed photoredox coupling of substituted N-aryltetrahydroisoquinolines (THIQs) and different bench-stable pyridinium salts was successfully developed to give fast access to 1-benzyl-THIQs. Furthermore, secondary alkyl and allyl groups were also successfully introduced via the same method. Additionally, the typically applied N-phenyl group in the THIQ substrate could be replaced by the cleavable p-methoxyphenyl (PMP) group and successful N-deprotection was demonstrated.
Highlights
The selective formation of new carbon–carbon bonds via direct C–H functionalization bears the potential of being a process of high efficiency [1,2,3]
We demonstrate the deaminative coupling of N-benzylpyridinium Katritzky salts with THIQs under ruthenium photoredox catalysis
We started our investigations by screening the coupling between N-phenyl-THIQ (1) with N-benzyl-(2,4,6-triphenyl)pyridinium tetrafluoroborate (2, Table 1; the complete optimization table can be found in Supporting Information File 1)
Summary
The selective formation of new carbon–carbon bonds via direct C–H functionalization bears the potential of being a process of high efficiency [1,2,3]. A ruthenium-catalyzed photoredox coupling of substituted N-aryltetrahydroisoquinolines (THIQs) and different bench-stable pyridinium salts was successfully developed to give fast access to 1-benzyl-THIQs. secondary alkyl and allyl groups were successfully introduced via the same method. We started our investigations by screening the coupling between N-phenyl-THIQ (1) with N-benzyl-(2,4,6-triphenyl)pyridinium tetrafluoroborate (2, Table 1; the complete optimization table can be found in Supporting Information File 1).
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