Nucleophilic perfluoroalkylation of imines and carbonyls: perfluoroalkyl sulfones as efficient perfluoroalkyl-transfer motifs

G K Surya Prakash; Ying Wang; Ryo Mogi; Jinbo Hu; Thomas Mathew; George A Olah

doi:10.1021/ol100918d

Nucleophilic perfluoroalkylation of imines and carbonyls: perfluoroalkyl sulfones as efficient perfluoroalkyl-transfer motifs

Org Lett. 2010 Jul 2;12(13):2932-5. doi: 10.1021/ol100918d.

Authors

G K Surya Prakash¹, Ying Wang, Ryo Mogi, Jinbo Hu, Thomas Mathew, George A Olah

Affiliation

¹ 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

PMID: 20518520
DOI: 10.1021/ol100918d

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Aldehydes / chemistry*
Alkylation
Amides / chemical synthesis*
Amides / chemistry
Imines / chemistry*
Ketones / chemistry*
Molecular Structure
Stereoisomerism
Sulfones / chemistry*

Substances

Aldehydes
Amides
Imines
Ketones
Sulfones