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Brønsted Acid Catalyzed C–H Functionalization of N ‐Protected Tetrahydroisoquinolines via Intermediate Peroxides
Author(s) -
SchweitzerChaput Bertrand,
Klussmann Martin
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201201527
Subject(s) - chemistry , surface modification , catalysis , brønsted–lowry acid–base theory , nucleophile , organocatalysis , organic chemistry , combinatorial chemistry , oxidative coupling of methane , enantioselective synthesis
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.