A Tin-Free, Radical Photocatalyzed Addition to Vinyl Sulfones

作者: Davide Ravelli , Sara Montanaro , Michele Zema , Maurizio Fagnoni , Angelo Albini

DOI: 10.1002/ADSC.201100591

关键词:

摘要: Radical conjugate addition onto vinyl sulfones was achieved by means of a convenient, tin-free procedure. This based on the photocatalyzed CH bond activation in aldehydes, amides, ethers and even cycloalkanes using tetrabutylammonium decatungstate (TBADT). The reaction likewise effective for functionalization β-substituted sulfones. products are useful building blocks were obtained satisfactory yields both under artificial UV light sunlight, so demonstrating “green” potential process.

参考文章(54)
Angelo Albini, Maurizio Fagnoni, The Greenest Reagent in Organic Synthesis: Light Springer, Dordrecht. pp. 173- 189 ,(2008) , 10.1007/978-1-4020-8457-7_8
Davide Ravelli, Daniele Dondi, Maurizio Fagnoni, Angelo Albini, Photocatalysis. A multi-faceted concept for green chemistry Chemical Society Reviews. ,vol. 38, pp. 1999- 2011 ,(2009) , 10.1039/B714786B
Maurizio Fagnoni, Daniele Dondi, Davide Ravelli, Angelo Albini, Photocatalysis for the formation of the C-C bond. Chemical Reviews. ,vol. 107, pp. 2725- 2756 ,(2007) , 10.1021/CR068352X
Davide Ravelli, Angelo Albini, Maurizio Fagnoni, Smooth Photocatalytic Preparation of 2‐Substituted 1,3‐Benzodioxoles Chemistry: A European Journal. ,vol. 17, pp. 572- 579 ,(2011) , 10.1002/CHEM.201002546
Hideo Togo, Masahiko Aoki, Masataka Yokoyama, Reductive addition to electron-deficient olefins with trivalent iodine compounds Tetrahedron. ,vol. 49, pp. 8241- 8256 ,(1993) , 10.1016/S0040-4020(01)88042-X
Carmen Nájera, Miguel Yus, Desulfonylation reactions: Recent developments Tetrahedron. ,vol. 55, pp. 10547- 10658 ,(1999) , 10.1016/S0040-4020(99)00600-6
Derek H.R. Barton, Hideo Togo, Samir Z. Zard, Radical addition to vinyl sulphones and vinyl phosphonium salts Tetrahedron Letters. ,vol. 26, pp. 6349- 6352 ,(1985) , 10.1016/S0040-4039(01)84596-2
Ilhyong Ryu, Shohei Uehara, Hidefumi Hirao, Takahide Fukuyama, Tin-free Giese reaction and the related radical carbonylation using alkyl iodides and cyanoborohydrides. Organic Letters. ,vol. 10, pp. 1005- 1008 ,(2008) , 10.1021/OL7031043
Martin Nielsen, Christian Borch Jacobsen, Nicole Holub, Marcio Weber Paixão, Karl Anker Jørgensen, Asymmetrische Organokatalyse mit Sulfonen Angewandte Chemie. ,vol. 122, pp. 2726- 2738 ,(2010) , 10.1002/ANGE.200906340