Brønsted Acid Catalyzed C–H Functionalization of N‐Protected Tetrahydroisoquinolines via Intermediate Peroxides. Issue 4 (13th December 2012)

• Record Type: Journal Article
• Authors: Schweitzer‐Chaput, Bertrand; Klussmann, Martin
• Is Part Of: European journal of organic chemistry. Issue 4(2013)
• Page Start: 666
• Page End: 671
• Publication Date: 2012-12-13
• Subjects: Peroxides -- C‐H activation -- Amines­ -- Homogeneous catalysis -- Brønsted acid catalysis; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201201527
• Languages: English
• ISSNs: 1434-193X

Abstract

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. Abstract : An organocatalytic oxidative synthesis of N ‐protected tetrahydroisoquinolines was achieved by C–H functionalization via Intermediate PeroxideS (CHIPS). The peroxides were synthesized under metal‐free thermal conditions and were converted into the final products by reaction with a variety of nucleophiles by using Brønsted acid catalysis.