Quaternary Ammonium Trifluoromethoxide Salts as Stable Sources of Nucleophilic OCF3

The reaction of nucleophilic tertiary amines with trifluoromethyl and pentafluoroethyl methyl ethers provides quaternary ammonium trifluoromethoxide (NR4OCF3) and pentafluoroethoxide (NR4OCF2CF3) salts, respectively, in good yields. The new trifluoromethoxide salts disclosed herein are uniquely stab...

Full description

Saved in:
Bibliographic Details
Published inOrganic letters Vol. 22; no. 5; pp. 1785 - 1790
Main Authors Newton, Josiah J, Jelier, Benson J, Meanwell, Michael, Martin, Rainer E, Britton, Robert, Friesen, Chadron M
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 06.03.2020
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ALKENES
POTENT
TETRAMETHYLAMMONIUM
TRIFLUOROMETHYLTHIOLATION
AMINES
DIAZO ESTERS
TRIFLUOROMETHYLSELENOLATION
ARYL IODIDES
Online AccessGet full text
ISSN1523-7060
1523-7052
1523-7052
DOI10.1021/acs.orglett.0c00099

Cover

More Information
Summary:The reaction of nucleophilic tertiary amines with trifluoromethyl and pentafluoroethyl methyl ethers provides quaternary ammonium trifluoromethoxide (NR4OCF3) and pentafluoroethoxide (NR4OCF2CF3) salts, respectively, in good yields. The new trifluoromethoxide salts disclosed herein are uniquely stable for extended periods of time in both the solid state and in solution, which complements contemporary reagents. Here we describe the preparation of a range of NR4OCF3 salts, their long-term stability, and utility in substitution reactions.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.0c00099