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Synthesis and Reactions of (2,2,2‐Trifluoroethyl)triphenylphosphonium Trifluoromethanesulfonate
Author(s) -
Hanamoto Takeshi,
Morita Noriko,
Shindo Keiko
Publication year - 2003
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200300395
Subject(s) - chemistry , trifluoromethanesulfonate , wittig reaction , yield (engineering) , hydrolysis , sodium hydroxide , organic chemistry , medicinal chemistry , base (topology) , methanol , catalysis , mathematical analysis , materials science , mathematics , metallurgy
(2,2,2‐Trifluoroethyl)triphenylphosphonium trifluoromethanesulfonate (triflate) ( 1 ) was readily synthesized in high yield from triphenylphosphane and 2,2,2‐trifluoroethyl triflate. The Wittig olefination of 1 with aromatic aldehydes bearing electron‐withdrawing groups with CsF as a base in DMF proceeded cleanly, producing the corresponding 3,3,3‐trifluoropropenylidene compounds in good yields. On the other hand, the hydrolysis of 1 in methanol containing sodium hydroxide gave (2,2‐dimethoxyvinyl)triphenylphosphonium triflate ( 6a ) in high yield instead of the corresponding (2,2,2‐trifluoroethyl)diphenylphosphane oxide. Furthermore, reactions between 1 and secondary amines exclusively gave the novel ( Z )‐(2‐amino‐2‐fluorovinyl)triphenylphosphonium triflates ( 10 ) in high yields. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)