- Addition of organolithium reagents to α-(trifluoromethyl)styrene: Concise synthesis of functionalised gem-difluoroalkenes
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The treatment of α-(trifluoromethyl)styrene with organolithium reagents results in the selective formation of gem-difluoroalkenes in good-to-excellent yields. This reaction has been applied to the synthesis of 3-gem-difluoro-2-phenylallylic amines and oth
- Begue, Jean-Pierre,Bonnet-Delpon, Daniele,Rock, Michael H.
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- Catalyzing the Hydrodefluorination of CF3-Substituted Alkenes by PhSiH3. H?Transfer from a Nickel Hydride
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The hydrodefluorination of CF3-substituted alkenes can be catalyzed by a nickel(II) hydride bearing a pincer ligand. The catalyst loading can be as low as 1 mol%. gem-Difluoroalkenes containing a number of functional groups can be formed in goo
- Hammond, Matthew,Norton, Jack,Wang, Shuai,Yao, Chengbo
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supporting information
p. 4793 - 4799
(2020/03/31)
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- Direct Difluoromethylenation of Carbonyl Compounds by Using TMSCF3: The Right Conditions
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A deoxygenative difluoromethylenation of carbonyl compounds has been developed by using readily available, inexpensive trifluoromethyltrimethylsilane, LiI, and PPh3. The presence of the Li+ion prevents the unproductive exhaustion of trifluoromethyltrimethylsilane (TMSCF3) by keeping the soluble free fluoride concentration in the reaction medium under control. The strategy of combining solvents to increase the reactivity and thereby reduce the reaction temperature and time is disclosed.
- Krishnamoorthy, Sankarganesh,Kothandaraman, Jotheeswari,Saldana, Jacqueline,Prakash, G. K. Surya
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supporting information
p. 4965 - 4969
(2016/10/26)
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- gem-Difluoroolefination of Diazo Compounds with TMSCF3 or TMSCF2Br: Transition-Metal-Free Cross-Coupling of Two Carbene Precursors
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A new olefination protocol for transition-metal-free cross-coupling of two carbene fragments arising from two different sources, namely, a nonfluorinated carbene fragment resulting from a diazo compound and a difluorocarbene fragment derived from Ruppert-Prakash reagent (TMSCF3) or TMSCF2Br, has been developed. This gem-difluoroolefination proceeds through the direct nucleophilic addition of diazo compounds to difluorocarbene followed by elimination of N2. Compared to previously reported Cu-catalyzed gem-difluoroolefination of diazo compounds with TMSCF3, which possesses a narrow substrate scope due to a demanding requirement on the reactivity of diazo compounds and in-situ-generated CuCF3, this transition-metal-free protocol affords a general and efficient approach to various disubstituted 1,1-difluoroalkenes, including difluoroacrylates, diaryldifluoroolefins, as well as arylalkyldifluoroolefins. In view of the ready availability of diazo compounds and difluorocarbene reagents and versatile transformations of 1,1-difluoroalkenes, this new gem-difluoroolefination method is expected to find wide applications in organic synthesis.
- Hu, Mingyou,Ni, Chuanfa,Li, Lingchun,Han, Yongxin,Hu, Jinbo
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supporting information
p. 14496 - 14501
(2015/11/27)
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- A Concise Synthesis of Functionalised gem-Difluoroalkenes via the Addition of Organolithium Reagents to α-Trifluoromethylstyrene
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The treatment of α-trifluoromethyl styrene with organolithium reagents results in the selective formation of gem-difluoroalkenes in good to excellent yield.This reaction has been applied to the synthesis of a range functionalised gem-difluoroalkenes. - Ke
- Begue, Jean-Pierre,Bonnet-Delpon, Daniele,Rock, Michael H.
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p. 5003 - 5006
(2007/10/02)
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- PREPARATION AND SYNTHETIC UTILITY OF FLUORINATED PHOSPHONIUM SALTS, BISPHOSPHONIUM SALTS AND PHOSPHORANIUM SALTS
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The reaction of tertiary phosphines with fluorohalomethanes provides a rapid and high yield synthesis of various types of fluorinated phosphonium salts, bis-phosphonium salts and phosphoranium salts.These salts are useful precursors to fluorine-containing
- Burton, Donald J.
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p. 339 - 358
(2007/10/02)
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