- Chemoselective Homologation-Deoxygenation Strategy Enabling the Direct Conversion of Carbonyls into (n+1)-Halomethyl-Alkanes
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The sequential installation of a carbenoid and a hydride into a carbonyl, furnishing halomethyl alkyl derivatives, is reported. Despite the employment of carbenoids as nucleophiles in reactions with carbon-centered electrophiles, sp3-type alkyl halides remain elusive materials for selective one-carbon homologations. Our tactic levers on using carbonyls as starting materials and enables uniformly high yields and chemocontrol. The tactic is flexible and is not limited to carbenoids. Also, diverse carbanion-like species can act as nucleophiles, thus making it of general applicability.
- Citarella, Andrea,Holzer, Wolfgang,Ielo, Laura,Langer, Thierry,Miele, Margherita,Pace, Vittorio,Urban, Ernst,Zehl, Martin
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supporting information
p. 7629 - 7634
(2020/10/12)
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- Fluoroanalogs of DDT: Superacidic BF3-H2O catalyzed facile synthesis of 1,1,1-trifluoro-2,2-diarylethanes and 1,1-difluoro-2,2- diarylethanes
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The one-pot synthesis of 1,1,1-trifluoro- and 1,1-difluoro-2,2- diarylethanes from arenes and fluorinated hemiacetals in the BF 3-H2O system is described. The reaction is simple, clean, and convenient, eliminating the use of organic
- Prakash, G. K. Surya,Paknia, Farzaneh,Mathew, Thomas,Mloston, Gzregorz,Joschek, Jens P.,Olah, George A.
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supporting information; experimental part
p. 4128 - 4131
(2011/10/04)
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- Rearrangements accompanying fluorination of 2-amino alcohols and 1,2-diols with Deoxo-Fluor
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2-Amino alcohols and 1,2-diols treated with Deoxo-Fluor in methylene chloride resulted in the formation of rearranged major products concomitantly with minor amounts of the straightforward fluorinated replacement products in good yields.
- Ye, Chengfeng,Shreeve, Jean'ne M.
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p. 1869 - 1872
(2007/10/03)
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- Reaction of epoxides with diethylaminosulfur triflouride
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Diethylaminosulfur triflouride (DAST) reacts with epoxides (oxiranes) to form geminal diflourides, vicinal diflourides, and bis(2-fluoroalkyl) ethers. Thus cyclopentene oxide gave cis-1,2-difluorocyclopentane and bis(2-fluorocyclopentyl) ether; cyclohexene oxide gave cis-1,1-difluorocyclohexane and bis(2-fluorocylohexyl) ether; styrene oxide gave 1,1-difluoroethylbenzene and 1,2-difluoroethylbenzene; and cis- and trans-stilbene oxides gave mixtures of meso- and racemic 1,2-difluoro-1,2-diphenylethanes together with 1,1-difluoro-2,2-diphenylethane resulting from a rearrangement. Cyclooctene oxide and cyclohexene sulfide do not react appreciably under the same conditions.
- Hudlicky, Milos
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p. 373 - 384
(2007/10/02)
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