123455-90-3Relevant academic research and scientific papers
Synthesis of trifluoromethyl-substituted cyclopropanes via sequential Kharasch-dehalogenation reactions
Risse, Julie,Fernández-Zúmel, Mariano A.,Cudré, Yanouk,Severin, Kay
, p. 3060 - 3063 (2012)
A two-step process for the synthesis of trifluoromethyl-substituted cyclopropanes is described. Halothane, an anesthetic agent, is added to olefins in a ruthenium-catalyzed Kharasch reaction. The resulting 1,3-dihalides are converted into cyclopropanes by dehalogenation with magnesium. This procedure represents an alternative to metal-catalyzed cyclopropanations involving trifluoromethyl diazomethane.
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.
NUCLEOPHILIC SUBSTITUTION REACTIONS OF DIFLUOROMETHYL PHENYL SULFONE WITH ALKYL HALIDES LEADING TO THE FACILE SYNTHESIS OF TERMINAL 1,1-DIFLUORO-1-ALKENES AND DIFLUOROMETHYLALKANES
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Page/Page column 11; 18, (2008/06/13)
(Benzenesulfonyl)difluoromethyl anion, in situ generated from difluoromethyl phenyl sulfone and a base, was found to easily undergo nucleophilic substitution reactions (SN2 with primary alkyl halides, elemental halogens, and perfluoroalkyl halides with good selectivity. The formed (Benzenesulfonyl) difluoromethylalkanes are useful intermediates for the facile preparation of 1,1-difluoro-1alkenes and difluoromethylalkanes. Thus, difluoromethyl phenyl sulfone acts as both “CF2=” and CF2H” synthons.
Difluoromethyl phenyl sulfone, a difluoromethylidene equivalent: Use in the synthesis of 1,1-difluoro-1-alkenes
Prakash, G.K. Surya,Hu, Jinbo,Wang, Ying,Olah, George A.
, p. 5203 - 5206 (2007/10/03)
A nucleophilic substitution-elimination reaction strategy in which difluoromethyl phenyl sulfone is used as a selective difluoromethylidene equivalent allows the facile synthesis of 1,1-difluoro-1-alkenes from primary alkyl halides (see scheme).
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.
Reactions of 2,2-difluoroalkenylboranes with halogens in the presence of base. Novel syntheses of symmetrically disubstituted 1,1-difluoro-1-alkenes and 1,1-difluoro-2-iodo-1-alkenes
Ichikawa,Sonoda,Kobayashi
, p. 6379 - 6382 (2007/10/02)
Treatment of 2,2-difluoroalkenylboranes with bromine and iodine causes coupling reaction and halogenolysis to afford the title compounds in a reverse manner to nonfluorinated counterpart.
