123455-91-4Relevant academic research and scientific papers
Coupling of Trifluoroacetaldehyde N-Triftosylhydrazone with Organoboronic Acids for the Synthesis of gem-Difluoroalkenes
Ma, Yu,Reddy, Bhoomireddy Rajendra Prasad,Bi, Xihe
supporting information, p. 9860 - 9863 (2019/12/24)
The synthesis of alkyl gem-difluoroalkenes remains a difficult task in organic synthesis. Here, we report a general and efficient approach for tackling this problem by gem-difluoroolefination of trifluoroacetaldehyde N-triftosylhydrazone with organoboronic acids. This protocol is operationally simple, free of transition metals, and suitable for a broad range of organoboronic acids. Moreover, the utility of the products was demonstrated by further conversion of the gem-difluorovinyl group.
Copper(I)-catalyzed stereoselective defluoroborylation of aliphatic gem-difluoroalkenes
Ito, Hajime,Seo, Tamae,Kojima, Ryoto,Kubota, Koji
supporting information, p. 1330 - 1332 (2018/10/15)
This study reports a method for the stereoselective copper(I)catalyzed defluoroborylation of aliphatic gem-difluoroalkenes to afford (Z)-monofluoro-substituted borylalkenes. Gem-difluoro-alkenes bearing a variety of functional groups were efficiently borylated with high stereoselectivity. A theoretical study of the reaction mechanism is also described.
Activation of 1,1-difluoro-1-alkenes with a transition-metal complex: Palladium(II)-catalyzed friedel - crafts-type cyclization of 4,4-(difluorohomoallyl)arenes
Yokota, Misaki,Fujita, Daishi,Ichikawa, Junji
, p. 4639 - 4642 (2008/03/15)
(Chemical Equation Presented) Cationic palladium(II) ([Pd(MeCN) 4](BF4)2) provides the first transition-metal-catalyzed method for electrophilic activation of electron-deficient 1,1-difluoro-1-alkenes, which allows their Friedel-Crafts-type cyclization with an intramolecular aryl group via a Wacker-type process. By using BF3·OEt2, the cyclization was effected by a catalytic amount of the palladium without its reoxidation.
Friedel-crafts cyclization of 1,1-difluoroalk-1-enes: Synthesis of benzene-fused cyclic ketones via α-fluorocarbocations
Ichikawa, Junji,Jyono, Hideharu,Kudo, Takao,Fujiwara, Masaki,Yokota, Misaki
, p. 39 - 46 (2007/10/03)
1,1-Difluoroalk-1-enes bearing a phenyl group at the C-3, -4, or -5 position, readily obtained from 2,2,2-trifluoroethyl p-toluenesulfonate, are treated with FSO3H·SbF5 to undergo Friedel-Crafts cyclization in (CF3)2CHOH. The cyclization takes place via α-fluorocarbocations, followed by spontaneous hydrolysis of the C-F bond to afford bicyclic ketones including a five, six, or seven-membered ring in good yield.
A NOVEL SYNTHESIS OF 1,1-DIFLUOROOLEFINS FROM 1,1,1-TRIFLUOROETHYL p-TOLUENESULFONATE VIA BORONATE-COMPLEX
Ichikawa, Junji,Sonoda, Takaaki,Kobayashi, Hiroshi
, p. 1641 - 1644 (2007/10/02)
The nucleophilic substitution of gem-difluorovinylic tosyloxy group with alkyl groups is effected by treating 2,2-difluoro-1-tosyloxyvinyllithium with trialkylboranes to afford 1,1-difluoroolefins in good yields.
