Microwave-enhanced ruthenium-catalysed atom transfer radical additions

[en] The first monomode microwave-assisted atom transfer radical additions (ATRA) of carbon tetrachloride to various olefins were successfully performed, affording the adducts with almost quantitative yields in less than 10 min at 160 'C. (c) 2007 Elsevier Ltd. All rights reserved.

Disciplines :

Chemistry

Author, co-author :

Borguet, Yannick ; Université de Liège - ULiège > Département de chimie (sciences) > Chimie macromoléculaire et catalyse organique

Richel, Aurore ; Université de Liège - ULiège > Gembloux Agro-Bio Tech > Gembloux Agro-Bio Tech

Delfosse, Sbastien

Leclerc, Alain

Delaude, Lionel ; Université de Liège - ULiège > Département de chimie (sciences) > Chimie macromoléculaire et catalyse organique

Demonceau, Albert ; Université de Liège - ULiège > Département de chimie (sciences) > Chimie macromoléculaire et catalyse organique

Language :

English

Title :

Microwave-enhanced ruthenium-catalysed atom transfer radical additions

Publication date :

2007

Journal title :

Tetrahedron Letters

ISSN :

0040-4039

Publisher :

Elsevier, Oxford, United Kingdom

Volume :

Issue :

Pages :

6334-6338

Peer reviewed :

Peer Reviewed verified by ORBi

Available on ORBi :

since 06 May 2009

Statistics

Number of views

72 (15 by ULiège)

Number of downloads

7 (3 by ULiège)

More statistics

Scopus citations^®

Scopus citations^®
without self-citations

OpenCitations

Bibliography

Kharasch M.S., Engelmann H., and Mayo F.R. J. Org. Chem. 2 (1938) 288
Kharasch M.S., Jensen E.V., and Urry W.H. Science 102 (1945) 128
Kato M., Kamigaito M., Sawamoto M., and Higashimura T. Macromolecules 28 (1995) 1721
Wang J.-S., and Matyjaszewski K. J. Am. Chem. Soc. 117 (1995) 5614
Matyjaszewski K., and Xia J. Chem. Rev. 101 (2001) 2921
Kamigaito M., Ando T., and Sawamoto M. Chem. Rev. 101 (2001) 3689
Simal F., Wlodarczak L., Demonceau A., and Noels A.F. Tetrahedron Lett. 41 (2000) 6071
Simal F., Wlodarczak L., Demonceau A., and Noels A.F. Eur. J. Org. Chem. (2001) 2689
Tutusaus O., Delfosse S., Simal F., Demonceau A., Noels A.F., Núñez R., Viñas C., and Teixidor F. Inorg. Chem. Commun. 5 (2002) 941
Tutusaus O., Viñas C., Núñez R., Teixidor F., Demonceau A., Delfosse S., Noels A.F., Mata I., and Molins E. J. Am. Chem. Soc. 125 (2003) 11830
Tutusaus O., Delfosse S., Demonceau A., Noels A.F., Viñas C., and Teixidor F. Tetrahedron Lett. 44 (2003) 8421
Simal F., Demonceau A., and Noels A.F. Tetrahedron Lett. 40 (1999) 5689
Simal F., Delfosse S., Demonceau A., Noels A.F., Denk K., Kohl F.J., Weskamp T., and Herrmann W.A. Chem. Eur. J. 8 (2002) 3047
Simal F., Demonceau A., and Noels A.F. Angew. Chem. 111 (1999) 559
Angew. Chem., Int. Ed. 38 (1999) 538
Simal F., Sebille S., Hallet L., Demonceau A., and Noels A.F. Macromol. Symp. 161 (2000) 73
Simal F., Jan D., Delaude L., Demonceau A., Spirlet M.-R., and Noels A.F. Can. J. Chem. 79 (2001) 529
Delaude L., Delfosse S., Richel A., Demonceau A., and Noels A.F. Chem. Commun. (2003) 1526
Richel A., Delfosse S., Cremasco C., Delaude L., Demonceau A., and Noels A.F. Tetrahedron Lett. 44 (2003) 6011
Richel A., Demonceau A., and Noels A.F. Tetrahedron Lett. 47 (2006) 2077
Delaude L., Demonceau A., and Noels A.F. Curr. Org. Chem. 10 (2006) 203
Sauvage X., Borguet Y., Noels A.F., Delaude L., and Demonceau A. Adv. Synth. Catal. 349 (2007) 255
Simal F., Sebille S., Demonceau A., Noels A.F., Nuñez R., Abad M., Teixidor F., and Viñas C. Tetrahedron Lett. 41 (2000) 5347
Delaude L., Demonceau A., and Noels A.F. Top. Organomet. Chem. 11 (2004) 155
Severin K. Curr. Org. Chem. 10 (2006) 217
Gedye R., Smith F., Westaway K., Ali H., Baldisera L., Laberge L., and Rousell J. Tetrahedron Lett. 27 (1986) 279
Giguere R.J., Bray T.L., Duncan S.M., and Majetich G. Tetrahedron Lett. 27 (1986) 4945
Perreux L., and Loupy A. Tetrahedron 57 (2001) 9199
Lidström P., Tierney J., Wathey B., and Westman J. Tetrahedron 57 (2001) 9225
Hayes B.L. Microwave Synthesis: Chemistry at the Speed of Light. 1st ed. (2002), CEM, Matthews, NC
Larhed M., Moberg C., and Hallberg A. Acc. Chem. Res. 35 (2002) 717
Kappe C.O. Angew. Chem. 116 (2004) 6408
Angew. Chem., Int. Ed. 43 (2004) 6250
Hayes B.L. Aldrichim. Acta 37 (2004) 66
Nüchter M., Ondruschka B., Bonrath W., and Gum A. Green Chem. 6 (2004) 128
Xu Y., and Guo Q.-X. Heterocycles 63 (2004) 903
Kappe C.O. Chimia 60 (2006) 308
Bose A.K., Manhas M.S., Ghosh M., Shah M., Raju V.S., Bari S.S., Newaz S.N., Banik B.K., Chaudhary A.G., and Barakat K.J. J. Org. Chem. 56 (1991) 6968
Olofsson K., Kim S.-Y., Larhed M., Curran D.P., and Hallberg A. J. Org. Chem. 64 (1999) 4539
Horikoshi S., Hidaka H., and Serpone N. Chem. Phys. Lett. 376 (2003) 475
Lamberto M., Corbett D.F., and Kilburn J.D. Tetrahedron Lett. 44 (2003) 1347
Wetter C., and Studer A. Chem. Commun. (2004) 174
Studer A., and Schulte T. Chem. Rec. 5 (2005) 27
Sherman E.S., Fuller P.H., Kasi D., and Chemler S.R. J. Org. Chem. 72 (2007) 3896
See also Ref. 11e:. Angew. Chem., Int. Ed. 43 (2004) 6268-6269
Adámek F., and Hájek M. Tetrahedron Lett. 33 (1992) 2039
Aidouni A., Demonceau A., and Delaude L. Synlett (2006) 493
Demonceau A., Delfosse S., Wei H., and Noels A.F. Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.) 46 (2005) 295
Delfosse S., Borguet Y., Delaude L., and Demonceau A. Macromol. Rapid Commun. 28 (2007) 492
Matsumoto H., Nakano T., and Nagai Y. Tetrahedron Lett. 14 (1973) 5147
Nagashima H., Ara K.-I., Wakamatsu H., and Itoh K. J. Chem. Soc., Chem. Commun. (1985) 518
Hayes T.K., Freyer A.J., Parvez M., and Weinreb S.M. J. Org. Chem. 51 (1986) 5503
Hayes T.K., Villani R., and Weinreb S.M. J. Am. Chem. Soc. 110 (1988) 5533
Nagashima H., Ozaki N., Seki K., Ishii M., and Itoh K. J. Org. Chem. 54 (1989) 4497
Lee G.M., and Weinreb S.M. J. Org. Chem. 55 (1990) 1281
Nagashima H., Wakamatsu H., Ozaki N., Ishii T., Watanabe M., Tajima T., and Itoh K. J. Org. Chem. 57 (1992) 1682
Guerrero-Sanchez C., Hoogenboom R., and Schubert U.S. Chem. Commun. (2006) 3797
With complex 1, the microwave-assisted Kharasch addition was accelerated by a factor 142.5 compared to the conventional addition at 85 °C, whereas with complex 2 the increase was limited to a factor 6.25 (see Supplementary Fig. S10).
Brown S.L., Rayner C.M., Graham S., Cooper A., Rannard S., and Perrier S. Chem. Commun. (2007) 2145