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.
Prakash
G K Surya
GK
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
Wang
Ying
Y
Mogi
Ryo
R
Hu
Jinbo
J
Mathew
Thomas
T
Olah
George A
GA
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