- gem-Difluoro Compounds: A Convenient Preparation from Ketones and Aldehydes by Halogen Fluoride Treatment of 1,3-Dithiolanes
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gem-Difluoro compounds can be prepared from ketones and aldehydes by formation of the corresponding 1,3-dithiolanes, followed by reaction with 1,3-dibromo-5,5-dimethylhydantoin and pyridinium poly(hydrogenfluoride) (HF-pyridine) in methylene chloride.The
- Sondej, Susan C.,Katzenellenbogen, John A.
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- Palladium-Catalyzed Negishi Cross-Coupling Reaction of Aryl Halides with (Difluoromethyl)zinc Reagent
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The palladium-catalyzed Negishi cross-coupling reaction of aryl iodides and bromides with (difluoromethyl)zinc reagent bearing a diamine such as TMEDA is achieved to provide the difluoromethylated aromatic compounds in good to excellent yields. The advantages of (difluoromethyl)zinc reagent are that (1) the derivatives, which possess different stability and reactivity, can be readily prepared via ligand screening and (2) transmetalation of a difluoromethyl group from the zinc reagent to palladium catalyst efficiently proceeds without an activator.
- Aikawa, Kohsuke,Serizawa, Hiroki,Ishii, Koki,Mikami, Koichi
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supporting information
p. 3690 - 3693
(2016/08/16)
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- Well-Defined, Shelf-Stable (NHC)Ag(CF2H) Complexes for Difluoromethylation
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The preparation of the thermally stable, well-defined NHC-ligated difluoromethylated silver complexes 1a,b is described. The complexes were fully characterized, and the structural assignments were ambiguously further confirmed by single-crystal X-ray diffraction. Reactions of [(SIPr)Ag(CF2H)] with a variety of activated electrophiles such as diaryliodonium salts, vinyl(aryl)iodonium salts, aryldiazonium salts, and acid chlorides in the presence or absence of CuI occurred smoothly at room temperature to generate difluoromethylated compounds in good to excellent yields. (Chemical Equation Presented).
- Gu, Yang,Chang, Dalu,Leng, Xuebing,Gu, Yucheng,Shen, Qilong
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p. 3065 - 3071
(2015/06/30)
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- Sandmeyer difluoromethylation of (hetero-)arenediazonium salts
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A Sandmeyer-type difluoromethylation process has been developed that allows the straightforward conversion of (hetero-)arenediazonium salts into the corresponding difluoromethyl (hetero-)arenes under mild conditions. The actual difluoromethylating reagent, a difluoromethyl-copper complex, is formed in situ from copper thiocyanate and TMS-CF2H. The diazonium salts are either preformed or generated in situ from broadly available aromatic amines.
- Matheis, Christian,Jouvin, Kvin,Goossen, Lukas J.
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supporting information
p. 5984 - 5987
(2015/01/08)
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