Pd(II)-catalyzed o-C-H acetoxylation of phenylalanine and ephedrine derivatives with MeCOOO(t)Bu/Ac2O.
Pd(II)-catalyzed ortho C-H acetoxylation of triflate protected phenethyl- and phenpropylamines has been achieved with tert-butyl peroxyacetate as the stoichiometric oxidant and either DMF or CH(3)CN as the promoter. The reaction was found to tolerate a large variety of functional groups and could be combined with subsequent intramolecular amination to afford functionalized indoline derivatives.
Vickers
Chris J
CJ
Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
Mei
Tian-Sheng
TS
Yu
Jin-Quan
JQ
D000586:Amination; D002384:Catalysis; D004809:Ephedrine / Q000031:analogs & derivatives* / Q000737:chemistry*; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010165:Palladium / Q000737:chemistry*; D010649:Phenylalanine / Q000031:analogs & derivatives* / Q000737:chemistry*
D007211:Indoles; D010649:Phenylalanine; D010165:Palladium; C057812:indoline; D004809:Ephedrine