- Meta Selective C-H Borylation of Sterically Biased and Unbiased Substrates Directed by Electrostatic Interaction
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An electrostatically directed meta borylation of sterically biased and unbiased substrates is described. The borylation follows an electrostatic interaction between the partially positive and negative charges between the ligand and substrate. With this strategy, it has been demonstrated that a wide number of challenging substrates, especially 4-substituted substrates, can selectively be borylated at the meta position. Moreover, unsubstituted substrates also displayed excellent meta selectivity. The reaction employs a bench-stable ligand and proceeds at a milder temperature, precluding the need to synthesize a bulky and sophisticated ligand/template.
- Chaturvedi, Jagriti,Haldar, Chabush,Bisht, Ranjana,Pandey, Gajanan,Chattopadhyay, Buddhadeb
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p. 7604 - 7611
(2021/05/26)
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- Trifluoroacetylation of amines with trifluoroacetic acid in the presence of trichloroacetonitrile and triphenylphosphine
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We developed a mild and convenient trifluoroacetylation process for amines using a combination of trichloroacetonitrile and triphenylphosphine. The reaction that we designed is applicable to the trifluoroacetylation of a wide variety of amines, including amines with stereogenic centers, which underwent trifluoroacetylation without racemization.
- Kim, Joong-Gon,Jang, Doo Ok
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scheme or table
p. 683 - 685
(2010/04/02)
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- A convenient trifluoroacetylation reagent: N- (trifluoroacetyl)succinimide
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N-(Trifluoroacetyl)succinimide, easily prepared from trifluoroacetic anhydride and succinimide forms a novel, convenient trifluoroacetylating reagent. It trifluoroacetylates alcohols, phenols and mines, to generate trifluoroacetate esters, and trifluoroacetamides in excellent yields with very efficient work up procedures.
- Katritzky, Alan R.,Yang, Baozhen,Guofang, Qiu,Zhang, Zhongxing
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- Electrolytic Reactions of Fluoroorganic Compounds. 14. Regioselective Anodic Methoxylation of N-(Fluoroethyl)amines. Preparation of Highly Useful Fluoroalkylated Building Blocks
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Anodic methoxylation of various types of N-(fluoroethyl)amines, ArRNCH2Rf (Rf = CF3, CHF2, CH2F, etc.) has been systematically studied and it was found that a methoxy group was exclusively or preferentially introduced into the position α to the fluoromethyl (Rf) group, depending on the Rf and R groups.The effect of the Rf group on the promotion of the anodic α-methoxylation decreased in the order CF3, CHF2, and CH2F.This remarkable promotion effect and unique regioselectivity can be explained mainly in terms of the α-CH kinetic acidities of the cation radicals formed by one-electron oxidation of the amines.The α-methoxylated products are highly useful precursors for the construction of carbon-carbon bonds α to the trifluoromethyl and difluoromethyl groups, which is difficult by other methods.
- Fuchigami, Toshio,Ichikawa,, Shinji
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p. 607 - 615
(2007/10/02)
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