Abstract
A new catalytic method for direct α-organylchalcogenation of aldehydes and ketones has been developed. When various aldehydes and ketones were allowed to react with diorganyl dichalcogenides in the presence of K3PO4, under mild reaction conditions, the corresponding α-organylseleno and α-arylthio aldehydes and ketones were obtained in good to high yields.
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References
Liotta D (1987) Organoselenium chemistry. Wiley, New York
Krief A (1991) In: Trost BM, Fleming I (eds) Comprehensive organic synthesis, vol 3. PergamonPress, Oxford, p 85
Back TG (1999) Organoselenium chemistry: a practical approach. Oxford University Press, New York
Abbas M, Bethke J, Wessjohann LA (2006) Chem Commun 541
Patai S, Rappoport Z (1986) The chemistry of organic selenium and tellurium compounds. Wiley, New York, vols 1 and 2 and references therein
Trost BM, Salzmann TN, Hiroi K (1976) J Am Chem Soc 98:4887
Kane V, Singh V, Martin A, Doyle DL (1983) Tetrahedron 39:345
Trost BM (1978) Chem Rev 78:363
Trost BM (1978) Acc Chem Res 11:453
Reich HJ, Renga JM, Reich IL (1975) J Am Chem Soc 97:5434
Sharpless KB, Young MW (1975) J Org Chem 40:947
Clive DL (1973) J Chem Soc Chem Commun 695
Shea RG, Fitzner JN, Fankhauser JE, Spaltenstein A, Carpino PA, Peevey RM, Pratt DV, Tenge BJ, Hopkins PB (1986) J Org Chem 51:5243
Fitzner JN, Shea RG, Fankhauser JE, Hopkins PB (1985) J Org Chem 50:417
Lerouge P, Paulmier C (1984) Tetrahedron Lett 25:1987
Miniejew C, Outurquin F, Pannecoucke X (2005) Tetrahedron 61:447
Lerouge P, Paulmier C (1984) Tetrahedron Lett 25:1983
Sunden H, Rios R, Cordova A (2007) Tetrahedron Lett 48:7865
Nicolaou KC, Claremon DA, Branette WE, Sitz SP (1979) J Am Chem Soc 101:3704
Wang J, Li H, Mei Y, Lou B, Xu D, Xie D, Guo H, Wang W (2005) J Org Chem 70:5678
Tiecco M, Carlone A, Sternativo S, Marini F, Bartoli G, Melchiorre P (2007) Angew Chem Int Ed 46:6882
Houllemare D, Ponthieux S, Outurquin F, Paulmier C (1997) Synthesis 101
Griacalone F, Gruttadauvia M, Marculescu AM, Noto R (2007) Tetrahedron Lett 48:255
Bao W, Zhang Y (1996) Synlett 1187
Nishiyama Y, Kawamatsu H, Funato S, Tokunaga K, Sonoda N (2003) J Org Chem 68:3599
Sharpless KB, Lauer RF (1973) J Am Chem Soc 95:2697
Huang X, Xu XH (1998) Synth Commun 28:807
Scholz D (1983) Synthesis 944
Seebach D, Teschner M (1973) Tetrahedron Lett 14:5113
Trost BM, Massiot GS (1977) J Am Chem Soc 99:4405
Groenewegen P, Kallenberg H, van der Gen A (1979) Tetrahedron Lett 20:2817
Coates RM, Pigott HD, Ollinger J (1974) Tetrahedron Lett 15:3955
Huang CH, Liao KS, De SK, Tsai YM (2000) Tetrahedron Lett 41:3911
Yadav JS, Suba Reddy BV, Jain R, Baishya G (2008) Tetrahedron Lett 49:3015
Nazari M, Movassagh B (2009) Tetrahedron Lett 50:1453
Victoria FN, Radatz CS, Sachini RM, Jacob RG, Perin G, da Silva WP, Lenardao EJ (2009) Tetrahedron Lett 50:6761
Nishiyama Y, Koguma Y, Tanaka T, Umeda R (2009) Molecules 14:3367
Movassagh B, Khosousi S (2012) Monatsh Chem 143:1503
Movassagh B, Alapour S (2013) J Sulf Chem 34:222
Zhao X, Yu Z, Yan S, Wu S, Liu R, He W, Wang L (2005) J Org Chem 70:7338
Kumar S, Engman L (2006) J Org Chem 71:5400
Pore DM, Soudagar MS, Desai OV, Thopate TS, Wadaganokar PP (2006) Tetrahedron Lett 47:9325
Hou X, Hemit H, Yong J, Nie L, Aisa HA (2010) Synth Commun 40:973
Niu J, Zhou H, Li Z, Xu J, Hu S (2008) J Org Chem 73:7814
Niu J, Guo P, Kang J, Li Z, Xu J, Hu S (2009) J Org Chem 74:5075
Balasubramaniam S, Aidhen IS (2011) Synlett 1533
Liotta D, Zima G, Barnum C, Sindane M (1980) Tetrahedron Lett 21:3643
Acknowledgments
Acknowledgment is made to the K. N. Toosi University of Technology Research Council for financial support of this study. The authors express their gratitude to Dr. Sogand Noroozizadeh for editing the English content of this manuscript.
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Movassagh, B., Yousefi, A. α-Organylchalcogenation of aldehydes and ketones with diorganyl dichalcogenides promoted by K3PO4 . Monatsh Chem 145, 1173–1177 (2014). https://doi.org/10.1007/s00706-014-1188-7
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DOI: https://doi.org/10.1007/s00706-014-1188-7