Solid-Phase Synthesis of (E)-3-Substituted Acrylonitriles from Polystyrene-Supported α-Selenoacetonitrile

REFERENCES

• For recent reviews, see ( a ) Shuttleworth , S. J. ; Allin , S. M. ; Wilson , R. D. ; Nasturica , D. Functionalised polymers in organic chemistry: Part 2 . Synthesis 2000 , ( 8 ), 1035 – 1074 ; ( b ) Sammelson , R. E. ; Kurth , M. J. Carbon–carbon bond-forming solid-phase reactions: Part II. Chem. Rev. 2001 , 101 ( 1 ), 137 – 202 ; ( c ) Blaney , P. ; Grigg , R. ; Sridharan , V. Traceless solid-phase organic synthesis . Chem. Rev. 2002 , 102 ( 7 ), 2607 – 2624 .
   Google Scholar
• Paulmier , C. (Ed.) Selenium Reagents and Intermediates in Organic Synthesis ; Pergamon Press : Oxford , 1986 .
   Google Scholar
• Reich , H. J. Functional group manipulation using organoselenium reagents . Acc. Chem. Res. 1979 , 12 ( 1 ), 22 – 30 .
   Web of Science ®Google Scholar
• (a) Krief , A. Synthetic methods using α-heterosubstituted organometallics . Tetrahedron 1980 , 36 ( 18 ), 2531 – 2640 ; (b) Rollinson , S. W. ; Amos , R. A. ; Katzenellenbogen , J. A. Total synthesis of Lauraceae lactones: Obtusilactones, litsenolides, and mahubanolides . J. Am. Chem. Soc. 1981 , 103 ( 14 ), 4114 – 4125 .
   Google Scholar
• (a) Nicolaou , K. C. ; Pastor , J. ; Barluenga , S. ; Winssinger , N. Polymer-supported selenium reagents for organic synthesis . Chem. Commun. 1998 , 18 , 1947 – 1948 : ( b ) Ruhland , T. ; Andersen , K. ; Pedersen , H. Selenium-linking strategy for traceless solid-phase synthesis: Direct loading, aliphatic C-H bond formation upon cleavage and reaction monitoring by gradient MAS NMR spectroscopy . J. Org. Chem. 1998 , 63 ( 25 ), 9204 – 9211 ; ( c ) Fujita , K.-I. ; Hashimoto , S. ; Oishi , A. ; Taguchi , Y. Intramolecular oxyselenenylation and deselenenylation reactions in water, conducted by employing polymer-supported arylselenenyl bromide . Tetrahedron Lett. 2003 , 44 ( 19 ), 3793 – 3795 ; ( d ) Mogemark , M. ; Gustafsson , L. ; Bengtsson , C. ; Elofsson , M. ; Kihlberg , J. A fluorinated selenide linker for solid-phase synthesis of n-pentenyl glycosides . Org. Lett. 2004 , 6 ( 26 ), 4885 – 4886 ; ( e ) Barrero , A. F. ; Quílez del Moral , J. F. ; Herrador , M. M. ; Herrador , M. M. ; Cortés , M. ; Arteaga , P. ; Catalán , J. V. ; Sánchez , E. M. ; Arteaga , J. F. Solid-phase selenium-catalyzed selective allylic chlorination of polyprenoids: Facile syntheses of biologically active terpenoids . J. Org. Chem. 2006 , 71 ( 15 ), 5811 – 5814 .
   Google Scholar
• (a) Dolter , R. J. ; Curran , C. Electric moments of some p-amino- and p-dimethylamino-β-styryl derivatives . J. Am. Chem. Soc. 1960 , 82 ( 16 ), 4153 – 4155 ; (b) André , L. ; Koffi , S. ; Jacqueline , S.-P. A stereoselective synthesis of trans-2-alkenenitriles . Synthesis 1977 , 2 , 126 – 127 ; (c) DiBiase , S. A. ; Lipisko , B. A. ; Haag , A. ; Wolak , R. A. ; Gokel , G. W. Direct synthesis of α,β-unsaturated nitriles from acetonitrile and carbonyl compounds: Survey, crown effects, and experimental conditions . J. Org. Chem. 1979 , 44 ( 25 ), 4640 – 4649 ; (d) Francoise , T.-B. ; André , F. The Wittig–Horner reaction in solid-liquid two-phase systems . Synthesis 1979 , 11 , 884 – 885 ; (e) Robinson , C. N. ; Horton , J. L. ; Foshee , D. O. ; Jones , J. W. ; Hanissian , S. H. ; Slater , C. D. Comparison of substituent constants for correlation of nuclear magnetic resonance absorptions of β-carbon atoms in ortho-substituted styrenes . J.Org. Chem. 1986 , 51 ( 18 ), 3535 – 3540 ; (f) Huang , X. ; Xie , L. ; Wu , H. Synthetic applications of organotellurium compounds, 1: A facile synthesis of α,β-unsaturated esters esters, ketones, and nitriles . J. Org. Chem. 1988 , 53 ( 20 ), 4862 – 4864 ; (g) Todres , Z. V. ; Ermekov , D. S. Behaviour of β-ferrocenylacrylonitrile in reactions with organic bases . J. Organomet. Chem. 1989 , 369 ( 3 ), 371 – 376 ; (h) Huang , Y.-Z. ; Liao , Y. Synthetic applications of elementoorganic compounds of group 15 and 16, 85: Pentaalkyl stiboranes, 1: Synthesis of homobenzylic alcohols, homoallylic alcohols, homoallylic alcohols, ethyl 5-aryl-5-hydroxy-2-pentenoates, and β-hydroxypropionic acid derivatives via pentaalkylstiboranes . J. Org. Chem. 1991 , 56 ( 4 ), 1381 – 1386 ; (i) Moreno-Mañas , M. ; Pleixats , R. ; Roglans , A. Stereospecific preparation of (E) and (Z)-3,3-diarylacrylonitriles by Heck reaction . Synlett 1997 , 10 , 1157 – 1158 ; (j) Rottländer , M. ; Boymond , L. ; Cahiez , G. ; Knochel , P. Stereoselective preparation of functionalized alkenylmagnesium reagents via an iodine-magnesium exchange reaction . J. Org. Chem. 1999 , 64 ( 4 ), 1080 – 1081 ; (k) Masllorens , J. ; Moreno-Mañas , M. ; Pla-Quintana , A. ; Pleixats , R. ; Roglans , A. Stereospecific synthesis of 3,3-disubstituted acrylonitriles by Heck reaction . Synthesis 2002 , ( 13 ), 1903 – 1911 ; (l) Kojima , S. ; Fukuzaki , T. ; Yamakawa , A. ; Murai , Y. Highly (Z)-selective synthesis of β-monosubstituted α,β-unsaturated cyanides using the Peterson reaction . Org. Lett. 2004 , 6 ( 22 ), 3917 – 3920 ; (m) Peppe , C. ; de Azevedo Mello , P. ; das Chagas , R. P. Indium (I) bromide–mediated coupling of dibromoacetonitrile with aldehydes followed by Boord elimination of bromine and oxygen of b-bromo alkoxides for preparation of 3-organyl-2-alkenenitriles . J. Organomet. Chem. 2006 , 691 ( 11 ), 2335 – 2339 .
   Google Scholar
• (a) Rappoport , Z. ( Ed.) Chemistry of the Cyano Group ; John Wiley & Sons : London , 1970; (b) Larock , R. C. Comprehensive Organic Transformations. A Guide to Functional Group Preparations ; VCH : New York , 1989.
   Google Scholar
• (a) Huang , X. ; Sheng , S.-R. A facile solid-phase synthesis of substituted 2(5H)-furanones from polymer-supported α-selenocarboxylic acids . J. Comb. Chem. 2003 , 5 ( 3 ), 273 – 277 ; ( b ) Sheng , S.-R. ; Zhou , W. ; Zhong , M.-H. ; Liu , X.-L. ; Song , C.-S. A facile method for solid-phase synthesis of vinyl sulfones using polystyrene-supported selenomethyl aryl sulfone . Synth. Commun. 2005 , 35 ( 6 ), 815 – 821 ; ( c ) Sheng , S.-R. ; Wang , Q.-Y. ; Huang , Y.-X. ; Xin , Q. ; Liu , X.-L. A facile solid-phase synthesis of aliphatic aldehydes using novel polymer-supported phenylselenomethyltrimethylsilane . Synth. Commun. 2006 , 36 ( 4 ), 429 – 434 ; ( d ) Sheng , S.-R. ; Huang , F.-F. ; Lin , S.-Y. ; Liu , X.-L. ; Huang , X. Solid-phase synthesis of 3-hydroxy-2-methylenealkanoates and their derivatives using polymer-supported α-phenylselenopropionate . Synthesis 2007 , (9) , 1373 – 1377 .
   PubMed Web of Science ®Google Scholar
• Zundel , G. Hydration structure and intermolecular interaction in polyelectrolytes . Angew. Chem., Int. Ed. Engl. 1969 , 8 ( 7 ), 499 – 509 .
   Google Scholar
• (a) Huang , X. ; Xu , W.-M. Polystyrene-supported benzyl selenide: An efficient reagent for highly stereocontrolled synthesis of olefins and allylic alcohols . Tetrahedron Lett. 2002 , 43 ( 31 ), 5495 – 5497 ; ( b ) Ferranti , F. ; De Filippo , D. A study of some benzeneseleninic acids: Kinetics of reduction by iodide ion . J. Chem. Soc. B 1971 , 1925 – 1927 .
   Google Scholar