- Nickel-Catalyzed Dimerization and Alkylarylation of 1,3-Dienes with Alkyl Fluorides and Aryl Grignard Reagents
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In the presence of a nickel catalyst, 1,3-butadiene undergoes selective dimerization and alkylarylation with alkyl fluorides and aryl Grignard reagents to give 1,6-octadienes with alkyl and aryl groups at the 3- and 8-positions, respectively, by the consecutive formation of three carbon-carbon bonds. The formation of an anionic nickel complex plays an important role in forming C-C bonds with alkyl fluorides.
- Iwasaki, Takanori,Min, Xin,Fukuoka, Asuka,Kuniyasu, Hitoshi,Kambe, Nobuaki
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p. 5550 - 5554
(2016/05/09)
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- Silver-catalyzed radical fluorination of alkylboronates in aqueous solution
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We report herein an efficient and general method for the deboronofluorination of alkylboronates. Thus, with the catalysis of AgNO3, the reactions of various alkylboronic acids or their pinacol esters with Selectfluor reagent in acidic aqueous solution afforded the corresponding alkyl fluorides under mild conditions. A broad substrate scope and wide functional group compatibility were observed. A radical mechanism is proposed for this site-specific fluorination.
- Li, Zhaodong,Wang, Zhentao,Zhu, Lin,Tan, Xinqiang,Li, Chaozhong
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p. 16439 - 16443
(2015/01/09)
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- A useful conversion of alcohols to alkyl fluorides
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A useful conversion of alcohols to alkyl fluorides via their fluoroformates is introduced. The fluoroformates are obtained in nearly quantitative yield from the alcohols by treatment with COF2 (generated in situ from bis(trichloromethyl) carbonate) in ether with KF as an added acid scavenger. The neat fluoroformates are cleaved to the fluorides by heating at 120-125°C using hexabutylguanidinium fluoride (HBGF) as the catalyst.
- Flosser, David A,Olofson, Roy A
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p. 4275 - 4279
(2007/10/03)
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- Approaches towards the synthesis of fluoro(cyclo)alkylamines
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The synthesis of fluoro(cyclo)alkylamines 1-amino-6-fluorohexane (1), 1-amino-7-fluoroheptane (2), cis/trans-4-fluorocyclohexylamine (3a,b) and cis-4-fluoromethylcyclohexylamine (4) has been investigated for use as synthons for histamine receptor ligands for use in PET.
- Windhorst,Bechger,Visser,Menge,Leurs,Timmerman,Herscheid
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- FLUORINATION OF HALOGENO ALCOHOLS WITH 1,1,2,3,3,3-HEXAFLUOROPROPYL DIETHYLAMINE
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Fluorination of halogeno alcohols with 1,1,2,3,3,3-hexafluoropropyl diethylamine (PPDA) was investigated. 2-Bromo-1-fluorobutane was obtained from the reaction of PPDA and 2-bromo-1-butanol (yield 50percent).Similar results were obtained from other alipha
- Watanabe, S.,Fujita, T.,Usui, Y.,Kimura, Y.
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p. 135 - 142
(2007/10/02)
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