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ÌâÄ¿£ºThe stereospecific preparation of (E)-1-aryl-F-1,3-butadienes

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The stereospecific preparation of (E)-1-aryl-F-1,3-butadienes



×÷Õß: Pedersen, SD (Pedersen, Scot D.)[ 1 ] ; Burton, DJ (Burton, Donald J.)[ 1 ]



À´Ô´³ö°æÎï: JOURNAL OF FLUORINE CHEMISTRY  ¾í:155   ÌØ¿¯:SI   Ò³:39-44   DOI:10.1016/j.jfluchem.2013.01.034   ³ö°æÄê:NOV 2013



±»ÒýƵ´Î: 0 (À´×Ô Web of Science)



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ÕªÒª: The Pd (PPh3) (4)/Cu(I)I catalyzed cross coupling of (Z)-1-tri-n-butylstanny1-1,2,3,4,4-pentafluoro-1,3-butadiene with substituted aryl iodides provides a useful stereospecific route to (E)-1-aryl-1,2,3,4,4-pentafluoro-1,3-butadienes. Substituents, such as 4-nitro, 2-nitro, H, 3-CF3, 3-OCH3, 2-CH3, 1-Pr-i react stereospecifically with the dienyl stannane synthon. Only with a bulky electron-withdrawing substuent, such as 2-CF3, did significant isomerization occur in isolation of the aryl diene. The bis-coupled product is formed stereospecifically with 1,4-diiodobenzene. The methodology could be extended to stereospecifically prepared the 1-triethylsilyl-1E,3E,-1,2,3,4,5,6,6-heptafluoro-1,3,5-hexatriene synthon. (C) 2013 Elsevier B.V. All rights reserved.



Èë²ØºÅ:WOS:000325447900004



ÎÄÏ×ÀàÐÍ: Article



ÓïÖÖ: English



×÷Õ߹ؼü´Ê: Polyfluorinated dienylstannanes; 1-Aryl-F-1,3-butadienes; Pd(0) cross-coupling reactions; 1-Triethyl-1E; 3E-1,2,3,4,5,6,6-heptafluoro-1,3,5-hexatriene synthon; (Z)-1-Tri-n-butyl-stannyl-1,2,3,4,4-pentafluoro-1,3-butadiene synthon



KeyWords Plus: STEREOSELECTIVE PREPARATION; (E)-2,3-DIFLUORO-3-STANNYLACRYLIC ESTER; COUPLING REACTIONS; SYNTHONS; DIENES



ͨѶ×÷ÕßµØÖ·: Burton, DJ (ͨѶ×÷Õß)




Univ Iowa, Dept Chem, Iowa City, IA 52242 USA.






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[ 1 ] Univ Iowa, Dept Chem, Iowa City, IA 52242 USA






µç×ÓÓʼþµØÖ·: donald-burton@uiowa.edu
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