Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2010(11): 1899-1904
DOI: 10.1055/s-0029-1218752
DOI: 10.1055/s-0029-1218752
SPECIALTOPIC
© Georg Thieme Verlag
Stuttgart ˙ New York
Magnesium Metal-Mediated Reductive Trifluoromethylation of Aldehydes with Phenyl Trifluoromethyl Sulfone
Further Information
Received
28 February 2010
Publication Date:
23 April 2010 (online)
Publication History
Publication Date:
23 April 2010 (online)
Abstract
An unprecedented reductive nucleophilic trifluoromethylation of aldehydes by using phenyl trifluoromethyl sulfone is reported. Mercury(II) chloride efficiently activates magnesium metal to induce the desulfonylative trifluoromethylation process. The new reductive trifluoromethylation provides an alternative method for efficient trifluoromethylation of non-enolizable or enolizable aldehydes with readily available phenyl trifluoromethyl sulfone reagent.
Key words
alkylations - aldehydes - alcohols - trifluoromethylations - phenyl trifluoromethyl sulfone
-
1a
Bégué J.-P.Bonnet-Delpon D. Bioorganic and Medicinal Chemistry of Fluorine Wiley-VCH; Weinheim: 2008. -
1b
Kirsch P. Modern Fluoroorganic Chemistry: Synthesis, Reactivity, Applications Wiley-VCH; Weinheim: 2004. -
1c
Organofluorine
Compounds: Chemistry and Applications, Yamamoto H.
Springer;
New
York:
2000.
-
1d
Ren J.Milton J.Weaver KL.Short SA.Stuart DI.Stammers DK. Structure 2000, 8: 1089 -
1e
Pedersen OS.Pedersen EB. Synthesis 2000, 479 -
1f
Price MLP.Jorgensen WL. J. Am. Chem. Soc. 2000, 122: 9455 -
1g
Böhm HJ.Banner D.Bendels S.Kansy M.Kuhn B.Müller K.Obst-Sander U.Stahl M. ChemBioChem 2004, 5: 637 -
1h
Jeschke P. ChemBioChem 2004, 5: 570 -
1i
Kirsch P.Bremer M. Angew. Chem. Int. Ed. 2000, 39: 4217 -
2a
Prakash GKS.Yudin AK. Chem. Rev. 1997, 97: 757 -
2b
Prakash GKS.Mandal M. J. Fluorine Chem. 2001, 112: 123 -
2c
Prakash GKS.Hu J. In Fluorine-Containing SynthonsSoloshonok VA. American Chemical Society; Washington DC: 2005. -
2d
Singh RP.Shreeve JM. Tetrahedron 2000, 56: 7613 -
2e
Langlois BR.Billard T. Tetrahedron 2003, 185 -
2f
McClinton MA.McClinton DA. Tetrahedron 1992, 48: 6555 -
2g
Burton DJ.Yang ZY. Tetrahedron 1992, 48: 189 -
2h
Médebielle M.Dolbier WR. J. Fluorine Chem. 2008, 129: 930 -
2i
Umemoto T. Chem. Rev. 1996, 96: 1757 -
2j
Ma J.-A.Cahard D. J. Fluorine Chem. 2007, 128: 975 -
2k
Ma J.-A.Cahard D. Chem. Rev. 2004, 104: 6119 -
2l
Shibata N.Mizuta S.Kawai H. Tetrahedron: Asymmetry 2008, 19: 2633 - For selected examples, see:
-
3a
Kitazume T.Ishikawa N. J. Am. Chem. Soc. 1985, 107: 5186 -
3b
Prakash GKS.Hu JB.Olah GA. J. Org. Chem. 2003, 68: 4457 -
3c
Large S.Roques N.Langlois BR. J. Org. Chem. 2000, 65: 8848 -
3d
Yokoyama Y.Mochida K. Synlett 1996, 1191 -
3e
Prakash GKS.Mandal M. J. Fluorine Chem. 2001, 112: 123 -
3f
Prakash GKS.Hu JB.Olah GA. Org. Lett. 2003, 5: 3253 -
3g
Joubert J.Roussel S.Christophe C.Billard T.Langlois BR.Vidal T. Angew. Chem. Int. Ed. 2003, 42: 3133 -
4a
Hu J. J. Fluorine Chem. 2009, 130: 1130 -
4b
Hu J.Zhang W.Wang F. Chem. Commun. (Cambridge) 2009, 7465 -
4c
Prakash GKS.Hu J. Acc. Chem. Res. 2007, 40: 921 -
5a
Yagupol’skii LM.Marenets MS. Zh. Obshch. Khim. 1954, 24: 887 -
5b
Lu TC. inventors; CN 1746155 (A). ; Chem. Abstr. 2006, 145, 103425 -
5c
Kremsner JM.Rack M.Pilger C.Kappe CO. Tetrahedron Lett. 2009, 50: 3665 -
5d
Chen Q.Duan J. J. Chem. Soc., Chem. Commun. 1993, 918 - 6
Nájera C.Yus M. Tetrahedron 1999, 55: 10547 - For selected examples, see:
-
7a
Trost BM.Neilsen JB.Hoogsteen K. J. Am. Chem. Soc. 1992, 114: 5432 -
7b
Mazéas D.Skrydstrup T.Beau JM. Angew. Chem. Int. Ed. 1995, 34: 909 -
7c
Jarreton O.Skrydstrup T.Beau JM. Tetrahedron Lett. 1997, 38: 1767 -
7d
Skrydstrup T.Jarreton O.Mazéas D.Urban D.Beau JM. Chem. Eur. J. 1998, 4: 655 -
7e
Krintel SL.Jiménez-Barbero J.Skrydstrup T. Tetrahedron Lett. 1999, 40: 7565 -
7f
Jarreton O.Skrydstrup T.Espinosa JF.Jiménez-Barbero J.Beau JM. Chem. Eur. J. 1999, 5: 430 -
7g
Katritzky AR.Feng DM.Qi M. J. Org. Chem. 1997, 62: 6222 -
7h
Dong JC.Kou BB.Li RT.Cheng TM. Synth. Commun. 2002, 32: 935 - For selected examples, see:
-
8a
Yu JR.Cho HS.Chandrasekhar S.Falck JR.Mioskowski C. Tetrahedron Lett. 1994, 35: 5437 -
8b
Yu JR.Cho HS.Falck JR. J. Org. Chem. 1993, 58: 5892 -
8c
Guijarro D.Yus M. Tetrahedron Lett. 1994, 35: 2965 -
8d
Alonso DA.Alonso E.Nájera C.Ramón DJ.Yus M. Tetrahedron 1997, 53: 4835 - 9
Lee GH.Choi EB.Lee E.Pak CS. Tetrahedron Lett. 1993, 34: 4541 - 10
Song JJ.Tan ZL.Reeves JT.Gallou F.Yee NK.Senanayake CH. Org. Lett. 2005, 7: 2193 - 11
Folleas B.Marek I.Normant JF.Saint-Jalmes L. Tetrahedron 2000, 56: 275 - 12
Chang Y.Cai C. Tetrahedron Lett. 2005, 46: 3161 - 13
Stewart R.Teo KC. Can. J. Chem. 1980, 58: 2491 - 14
Isao K,Takayuki H,Shoji T,Masayoshi M,Chizu S,Takeshi T, andKoichi F. inventors; EP 0434297. - 15
Xu Q.Zhou H.Geng XH.Chen PR. Tetrahedron 2009, 65: 2232 - 16
Shechter H.Conrad F. J. Am. Chem. Soc. 1950, 72: 3371 - 17
Kuwano R.Kondo Y.Shirahama T. Org. Lett. 2005, 7: 2973