Solvent-free anti-markovnikov addition of thiols to alkenes using anhydrous cerium(III) chloride as catalyst

Synlett

Volumn , Issue 5, 2010, Pages 790-792

  Silveira, Claudio C ^a   Mendes, Samuel R ^a   Líbero, Francieli M ^a  

^a FEDERAL UNIVERSITY OF SANTA MARIA   (Brazil)

Author keywords

Anti Markovnikov addition; Cerium(III) chloride; Green chemistry; Solvent free reaction

Indexed keywords

ALKENE DERIVATIVE; CERIUM; CERIUM CHLORIDE; THIOL DERIVATIVE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CATALYST; REACTION TIME; ROOM TEMPERATURE; SYNTHESIS;

EID: 77749280606     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1219350     Document Type: Article

References (17)

1. Peach M E., Thiols as Nucleophiles, In The Chemistry of the Thiol Group, Patai S, John Wiley & Sons London 1979 721 Organic Sulfur Chemistry, Oae S, CRC Press Boca Raton 1991
2. Cremlyn R J., An Introduction to Organo-Sulfur Chemistry Wiley & Sons New York 1996
3. Curran D P., In Comprehensive Organic Synthesis Vol. 4, Trost B M., Fleming I, Pergamon New York 1991 715
4. Protic acids:, Posner T, Ber. Dtsch. Chem. Ges. 1905 38 646, Screttas C G., Micha-Screttas M, J. Org. Chem. 1979 44 713, Wolf F, Finke H, Z. Chem. 1972 12 180
5. Lewis acids:, Mukaiyama T, Izawa T, Saigo K, Takai H, Chem. Lett. 1973 355, Belley M, Zamboni R, [nl]J. Org. Chem. 1989 54 1230, Kanagasabapathy S, Sudalai A, Benicewicz B C., Tetrahedron Lett. 2001 42 3791
6. Kumar P, Pandey R K., Hedge V R., Synlett 1999 1921
7. Banerjee S, Das J, Santra S, Tetrahedron Lett. 2009 50 124
8. Ranu B C., Mandal T, Synlett 2007 925
9. Griesbaum K, Angew. Chem., Int. Ed. Engl. 1970 9 273
10. Nicolaou G, Elemes Y, Tetrahedron Lett. 2008 49 6324
11. Sabitha G, Yadav J S., In Encyclopedia of Reagents for Organic Synthesis, Paquette L A., Wiley-VCH Weinheim 2006, Bartoli G, DiAntonio G, Giovannini R, Giuli S, Lanari S, Paoletti M, Marcantoni E, J. Org. Chem. 2008 73 1919, Yadav [nl]J S., SubbaReddy B V., SureshReddy Ch, Krishna [nl]A D., Tetrahedron Lett. 2007 48 2029, Meng Q, Sun Y, Ratovelomanana-Vidal V, Genêt J P., Zhang Z, J. Org. Chem. 2008 73 3842
12. Silveira C C., Mendes S R., Libero F M., Lenardão E J., Perin G, Tetrahedron Lett. 2009 50 6060, Silveira C C., Mendes S R., Tetrahedron Lett. 2007 48 7469, Silveira C C., Felix L A., Braga A L., Kaufman T S., Org. Lett. 2005 7 3701, Silveira C C., Bernardi C R., Braga A L., Kaufman T S., Tetrahedron Lett. 2003 44 6137
13. Cerium chloride was dried according to:, Dimitrov V, Kostova K, Genov M, Tetrahedron Lett. 1996 37 6787
14. Verma A K., Singh J, Chaudhary R, Tetrahedron Lett. 2007 48 7199
15. Fernández-Rodríguez M A., Hartwig J F., J. Org. Chem. 2009 74 1663
16. Movassagh B, Navidi M, ARKIVOC 2008 (xv) 47
17. Gajare A S., Sabde D P., Shingare M S., Wakharkar [nl]R D., Synth. Commun. 2007 32 1549