By Vadim A. Soloshonok
The booklet includes 35 top-notch chapter-reviews on contemporary methodological advancements within the quarter of man-made fluoro-organic chemistry in line with fluorinated synthons method. specific emphases are given to the synthesis of biologically suitable compounds (alcohols, amines, alpha- and beta-amino acids, peptides), industrial-scale creation of hugely flexible, synthetically beneficial fluorinated synthons, in addition to uneven synthesis of fluorinated synthons. The booklet has been designed to be a entire snap-shot of present examine job within the box reviewed through across the world popular best specialists from educational and business laboratories around the globe. the subjects coated within the e-book diversity from synthesis of small fluorinated molecules to peptides and macromolecules for crystal engineering. massive volume of knowledge reviewed within the booklet have by no means been released. particularly cutting-age expertise from business laboratories, summarized within the booklet, will supply the reader exceptional potential on advertisement availability of number of structurally varied fluorinated synthons that allows you to be on industry within the nearest destiny. taking into consideration the numerous impression that fluorinated compounds have made on approximately all features of contemporary existence this ebook is anticipated to be a present best reference within the box and can be of curiosity to varied readership.
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Extra resources for Fluorine-Containing Synthons
1 9 Yields were determined by F NMR based on the amount of 30a used. l Besides BuOK, sodium methoxide (CH ONa) and potassium hydroxide (KOH) were tried as nucleophiles (Table 3, entries d and e). Both of them worked but gave lower yields. There are several possible reasons: first of all, both sodium methoxide and KOH can not readily dissolve in DMF, which affects the reaction rate. Second, unlike potassium fBuOK, sodium methoxide may react with benzaldehyde via a Meerwein-Ponndorf-Verley type reduction pathway.
3 33 It is also possible that an alternative Barbier type coupled intermediate 30d is formed, which can generate the trimethylsilyldifluoromethyl radical species 36 that homo-couples to produce 32j. Likelihood of path Β was supported by the experimental result that, under similar reaction conditions using Mg and TMSC1 in DMF, both sulfone 32d (PhS0 CF SiMe ) and bissulfone 32e (PhS0 CF 0 SPh) readily produce compound 32j in good yields (Scheme 16). ch002 2 • 3 PhS0 CF SiMe 2 321 PhSCF H 2 N a H ° H0 2 (I) 3 30d » PhS0 CF SPh 2 » 2 (PhS0 ) CF 2 2 2 (II) 2 30e PhS0 CF SiMe 2 2 25% 70% 3 30d Mg/TMSCI DMF (PhS0 ) CF 2 2 2 • 30e Me SiCF CF SiMe 3 2 2 3 Me SiCF SiMe 3 2 32J 32k 79% 8% 3 (III) Scheme 16.
M . ; Larivee, A. Synthesis 2003, 11, 1693-1698. 27. Prakash, G. K. ; Mandal. M . ; Olah, G. J. Fluorine Chem. 2003, 123, 61-63; and the references therein. 28. (a) Sosnovskikh, V. ; Sevenard, D. ; Usachev, B. V. Tetrahedron Lett. 2003, 44, 2097-2099. (b) Sosnovskikh, V . Y . ; Usachev, Β. ; Sevenard, D. -V. J. Org. Chem. 2003, 68, 7747-7754. 29. Sevenard, D. ; Sosnovskikh, V. ; Kolomeitsev, Α. ; Konigsmann, M . , Tetrahedron Lett. 2003, 44, 7623-7627. 30. Singh, R. ; Shreeve, J. M . Chem. Comm.