Facile Solid‐Phase Synthesis of Aliphatic Aldehydes Using Novel Polymer‐Supported Phenylselenomethyltrimethylsilane

References

• Shuttleworth , S. J. , Allin , S. M. and Sharma , P. K. 1997 . Functionalized polymers: Recent developments and new application in synthetic organic chemistry . Synthesis , : 1217
   Google Scholar
• Guillier , F. , Orain , D. and Bradley , M. 2000 . Linkers and cleavage strategies in solid‐phase organic synthesis and combinatorial chemistry . Chem. Rev. , 100 : 2091
   PubMed Web of Science ®Google Scholar
• Sammelson , R. E. and Kurth , M. J. 2001 . Carbon–carbon bond‐forming solid‐phase reactions. Part II . Chem. Rev. , 101 : 137
   PubMed Web of Science ®Google Scholar
• Burnin , B. A. 1998 . The Combinatorial Index , CA 5 San Diego : Academic Press .
   Google Scholar
• Larock , R. C. 1999 . Comprehensive Organic Transformations—A Guide to Functional Group Preparations , 2nd ed. 1222 – 1225 . New York : Wiley‐VCH .
   Google Scholar
• Sachdev , K. and Sachdev , H. S. 1976 . A new reagent for aldehyde synthesis. 1‐Trimethylsilyl‐1‐phenylselenomethyllithium, a synthetic equivalent of formal carbanions . Tetrahedron Lett. , 17 : 4223
   Google Scholar
• Nicolaou , K. C. , Pastor , J. , Barluenga , S. and Winssinger , N. 1998 . Polymer‐supported selenium reagents for organic synthesis . Chem. Commun. , : 1947
   Web of Science ®Google Scholar
• Ruhland , T. , Andersen , K. and Pedersen , H. 1998 . 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. , 63 : 9204
   Web of Science ®Google Scholar
• Fujita , K. , Watanabe , K. , Oishi , A. , Ikeda , Y. and Taguchi , Y. 1990 . Preparation of polymer‐supported selenocyanates and their applications in solid‐phase oxyselenenylation‐deselenenylation . Synlett , : 1760
   Google Scholar
• Uehlin , L. and Wirth , T. 2001 . Novel polymer‐bound chiral selenium electrophiles . Org. Lett. , 3 : 2931
   PubMed Web of Science ®Google Scholar
• Huang , X. and Sheng , S.‐R. 2003 . A facile solid‐phase synthesis of substituted 2(5H)‐furanones from polymer‐supported α‐selenocarboxylic acids . J. Comb. Chem. , 5 : 805
   Google Scholar
• Sheng , S.‐R. , Wang , X.‐C. , Liu , X.‐L. and Song , C.‐S. 2003 . Selenium‐linking strategy for traceless solid‐phase synthesis of acrylamides . Synth. Commun. , 33 : 2867
   Web of Science ®Google Scholar
• Sheng , S.‐R. , Zhou , W. , Liu , X.‐L. and Song , C.‐S. 2004 . A convenient selenium‐linking strategy for traceless solid‐phase synthesis of diethyl 1‐alkenephosphonates . Synth. Commun. , 34 : 1011
   Web of Science ®Google Scholar
• Sheng , S.‐R. , Luo , H.‐R. W. , Zhong , M.‐H. , Liu , X.‐L. and Chen , H.‐Z. 2005 . A facile method for solid‐phase synthesis of vinyl sulfones using polystyrene‐supported selenomethyl aryl sulfone . Synth. Commun. , 35 : 847
   Web of Science ®Google Scholar
• Zundel , G. 1969 . Hydration structure and intermolecular interaction in polyelectrolytes . Angew. Chem., Int. Ed. Engl. , 8 : 499
   Web of Science ®Google Scholar
• Lethbridge , A. , Norman , R. O. C. and Thomas , C. B. 1973 . Reactions of lead(IV). Part XXVII. Oxidative rearrangement of styrene and related compounds to aldehydes or ketones in the presence of trifluoroacetic acid . J. Chem. Soc., Perkin Trans. 1 , : 35
   Google Scholar
• Ried , W. , Deuschel , A. and Kotelko , A. 1961 . Homologe aldehyde durch hydrogenolytische spaltung von N1‐acyl‐3, 5‐dimethyl‐pyrazolen . Liebigs. Ann. Chem. , 642 : 121
   Google Scholar
• Savoia , D. , Trombini , C. and Umani‐Ronchi , A. 1978 . Potassium–graphite as a metalation reagent synthesis of aldehydes and ketones by alkylation of imine and dihydro‐1, 3‐oxazine . J. Org. Chem. , 43 : 2907
   Web of Science ®Google Scholar
• Kocienski , P. J. 1980 . Phenylthiomethyltrimethylsilane: A new formyl anion synthon . Tetrahedron Lett. , 21 : 1559
   Web of Science ®Google Scholar