Nucleophilic perfluoroalkylation of imines and carbonyls: perfluoroalkyl sulfones as efficient perfluoroalkyl-transfer motifs.
Alkoxide-induced nucleophilic pentafluoroethylation and trifluoromethylation of aldehydes, ketones, and imines using pentafluoroethyl phenyl sulfone (PhSO(2)CF(2)CF(3), 1) and trifluoromethyl phenyl sulfone (PhSO(2)CF(3), 2), respectively, have been successfully achieved. High diastereoselectivity was observed during the perfluoroalkylation of homochiral sulfinimines to give the corresponding perfluoroalkyl sulfinamides.
Donald P. and Katherine B. Loker hydrocarbon Research Institute and Department of Chemistry, University of Southern California, Los Angeles, California 90089-1661, USA. gprakash@usc.edu
G K Surya
GK
Prakash
Ying
Y
Wang
Ryo
R
Mogi
Jinbo
J
Hu
Thomas
T
Mathew
George A
GA
Olah
D000447:Aldehydes / Q000737:chemistry*; D000478:Alkylation; D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry; D007097:Imines / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D013450:Sulfones / Q000737:chemistry*
D000447:Aldehydes; D000577:Amides; D007097:Imines; D007659:Ketones; D013450:Sulfones