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Brønsted acid-catalyzed C-H Functionalisation of N-Protected Tetrahydroisoquinolines via Intermediate Peroxides

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http://pubman.mpdl.mpg.de/cone/persons/resource/persons58987

Schweitzer-Chaput,  Bertrand
Research Group Klußmann, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

http://pubman.mpdl.mpg.de/cone/persons/resource/persons58702

Klußmann,  Martin
Research Group Klußmann, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Schweitzer-Chaput, B., & Klußmann, M. (2013). Brønsted acid-catalyzed C-H Functionalisation of N-Protected Tetrahydroisoquinolines via Intermediate Peroxides. European Journal of Organic Chemistry, 2013(4), 666-671. doi:10.1002/ejoc.201201527.


Cite as: http://hdl.handle.net/11858/00-001M-0000-0014-A517-D
Abstract
An organocatalytic oxidative synthesis of N-protected tetrahydroisoquinolines is described by C–H functionalization via intermediate peroxides. The peroxides were synthesized from tert-butylhydroperoxide under metal-free thermal conditions and were converted into the final products by Brønsted acid catalyzed substitution. The nucleophile scope was investigated in detail and proved to be broad; N-deprotection of the coupling products could also be achieved.