α-MsO/TsO/Cl ketones as oxidized alkyne equivalents: redox-neutral rhodium(III)-catalyzed C-H activation for the synthesis of N-heterocycles.
α-Halo and pseudohalo ketones are used for the first time as C(sp(3))-based electrophiles in transition-metal-catalyzed C-H activation and as oxidized alkyne equivalents in Rh(III)-catalyzed redox-neutral annulations to generate diverse N-heterocycles. This transformation is efficient and scalable. Due to the mild reaction conditions, a variety of functional groups could be tolerated.
Westfälische Wilhelms-Universität Münster, Organisch-Chemisches Institut, Corrensstrasse 40, 48149 Münster (Germany) http://www.uni-muenster.de/Chemie.oc/glorius/
Da-Gang
DG
Yu
Francisco
F
de Azambuja
Frank
F
Glorius
D000480:Alkynes / Q000737:chemistry*; D001557:Benzenesulfonates / Q000737:chemistry*; D002384:Catalysis; D002712:Chlorides / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D008698:Mesylates / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D012238:Rhodium / Q000737:chemistry*
D000480:Alkynes; D001557:Benzenesulfonates; D002712:Chlorides; D006571:Heterocyclic Compounds; D008698:Mesylates; C045880:methanesulfonic acid; D012238:Rhodium; C029501:4-toluenesulfonic acid
CH activation; N-heterocycles; isoquinolones; ketones; rhodium catalysis