- Palladium-catalyzed cross-coupling of unactivated alkylzinc reagents with 2-bromo-3,3,3-trifluoropropene and its application in the synthesis of fluorinated amino acids
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A palladium-catalyzed cross-coupling of unactivated alkylzinc reagents with 2-bromo-3,3,3-trifluoropropene (BTP) has been developed, which was used as a key step to prepare a series of trifluoromethylated and difluoromethylated amino acids that are of great interest in peptide/protein based chemical biology. The advantages of the synthesis of these fluorinated amino acids are synthetic simplicity and diversity from a simple and readily available key intermediate α-trifluoromethylalkene-containing amino acid, providing a facile route for applications in medicinal chemistry and life science.
- Lou, Yue-Guang,Wang, An-Jun,Zhao, Liang,He, Lin-Feng,Li, Xiao-Fei,He, Chun-Yang,Zhang, Xingang
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supporting information
p. 3705 - 3708
(2019/04/01)
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- Photoredox Generation of Carbon-Centered Radicals Enables the Construction of 1,1-Difluoroalkene Carbonyl Mimics
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Described is a facile, scalable route to access functional-group-rich gem-difluoroalkenes. Using visible-light-activated catalysts in conjunction with an arsenal of carbon-radical precursors, an array of trifluoromethyl-substituted alkenes undergoes radical defluorinative alkylation. Nonstabilized primary, secondary, and tertiary radicals can be used to install functional groups in a convergent manner, which would otherwise be challenging by two-electron pathways. The process readily extends to other perfluoroalkyl-substituted alkenes. In addition, we report the development of an organotrifluoroborate reagent to expedite the synthesis of the requisite trifluoromethyl-substituted alkene starting materials.
- Lang, Simon B.,Wiles, Rebecca J.,Kelly, Christopher B.,Molander, Gary A.
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supporting information
p. 15073 - 15077
(2017/11/20)
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- α-Trifluoromethyl-Destabilized Cations. A Route to 1-(Trifluoromethyl)tetralins by Trifluoroactolysis of 5-Aryl-1,1,1,-trifluoropentan-2-ols and Derivatives
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Trifluoroacetolysis of 5-aryl-1,1,1-trifluoropentan-2-ols 1 and their 2-aryl (2) and 2-methyl (3) analogues has been studied in search of a route to 1-(trifluoromethyl)tetralins.The results reflect the relative stabilities of the incipient carbocation int
- Bonnet-Delpon, Daniele,Cambillau, Christian,Charpentier-Morize, Micheline,Jacquot, Roland,Mesureur, Dany,Ourevitch, Michele
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p. 754 - 759
(2007/10/02)
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