Oxidative C-H bond functionalization and ring expansion with TMSCHN2 : a copper(I)-catalyzed approach to dibenzoxepines and dibenzoazepines.
Tricyclic dibenzoxepines and dibenzazepines are important therapeutic agents for the pharmaceutical industry and academic research. However, their syntheses are generally rather tedious, requiring several steps that involve a Wagner-Meerwein-type rearrangement under harsh conditions. Herein, we present the first copper(I)-catalyzed oxidative CH bond functionalization and ring expansion with TMSCHN2 to yield these important derivatives in a facile and straightforward way.
Organisch-Chemisches Institut, Universität Münster, 48149 Münster (Germany).
Tobias
T
Stopka
Leyre
L
Marzo
Mercedes
M
Zurro
Simon
S
Janich
Ernst-Ulrich
EU
Würthwein
Constantin G
CG
Daniliuc
José
J
Alemán
Olga García
OG
Mancheño
D001381:Azepines / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry; D002384:Catalysis; D056831:Coordination Complexes / Q000737:chemistry; D003300:Copper / Q000737:chemistry*; D003978:Diazomethane / Q000031:analogs & derivatives* / Q000737:chemistry; D003990:Dibenzoxepins / Q000737:chemistry; D006859:Hydrogen / Q000737:chemistry; D010084:Oxidation-Reduction; D013816:Thermodynamics; D014297:Trimethylsilyl Compounds / Q000737:chemistry*
D001381:Azepines; D056831:Coordination Complexes; D003990:Dibenzoxepins; D014297:Trimethylsilyl Compounds; D003978:Diazomethane; D002244:Carbon; D003300:Copper; D006859:Hydrogen; C060070:trimethylsilyldiazomethane
CH functionalization; TMSCHN2; copper; heterocycles; ring expansion