Synthesis of New N-Pyrrolylphosphane and Its Application in Hydroformylation of 1-Octene

L. Zhang; C. Li; X.L. Zheng; R.X. Li; H. Chen

doi:10.14233/ajchem.2015.17973

Issue

Vol. 27 No. 4 (2015): Vol 27 Issue 4

Issue Published : February 4, 2015

This work is licensed under a Creative Commons Attribution 4.0 International License.

Synthesis of New N-Pyrrolylphosphane and Its Application in Hydroformylation of 1-Octene

https://doi.org/10.14233/ajchem.2015.17973

L. Zhang

Key lab of Green Chemistry and Technology, Ministry of Education; College of Chemistry, Sichuan University, Chengdu 610064, P.R. China

C. Li

Key lab of Green Chemistry and Technology, Ministry of Education; College of Chemistry, Sichuan University, Chengdu 610064, P.R. China

X.L. Zheng

Key lab of Green Chemistry and Technology, Ministry of Education; College of Chemistry, Sichuan University, Chengdu 610064, P.R. China

R.X. Li

Key lab of Green Chemistry and Technology, Ministry of Education; College of Chemistry, Sichuan University, Chengdu 610064, P.R. China

H. Chen

Key lab of Green Chemistry and Technology, Ministry of Education; College of Chemistry, Sichuan University, Chengdu 610064, P.R. China

Corresponding Author(s) : H. Chen

scuhchen@163.com

Asian Journal of Chemistry, Vol. 27 No. 4 (2015): Vol 27 Issue 4
Article Published : February 4, 2015

Abstract

A new bidentate N-pyrrolylphosphane (1) which possessing strong p-acceptor property has been synthesized and applied in homogeneous rhodium-catalyzed hydroformylation of 1-octene. The effects of ligand/metal ratio, temperature, pressure and substrate/rhodium ratio on regioselectivity and activity were evaluated. The influence of the ligands (1 and 2) steric property on regioselectivity and activity in the hydroformylation of 1-octene was discussed. It was found that ligand 1 possess stronger chelating ability with rhodium than ligand 2 and always afforded higher regioselectivity and activity.

Keywords

Homogeneous catalysis Hydroformylation N-Pyrrolylphosphane Rhodium catalyst π-Acceptor

Zhang, L., Li, C., Zheng, X., Li, R., & Chen, H. (2015). Synthesis of New N-Pyrrolylphosphane and Its Application in Hydroformylation of 1-Octene. Asian Journal of Chemistry, 27(4), 1371–1374. https://doi.org/10.14233/ajchem.2015.17973

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References

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L.A. Van der Veen, M.D.K. Boele, F.R. Bregman, P.C.J. Kamer, P.W.N.M. van Leeuwen, K. Goubitz, J. Fraanje, H. Schenk and C. Bo, J. Am. Chem. Soc., 120, 11616 (1998); doi:10.1021/ja981969e.
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References

A.M. Trzeciak and J.J. Ziolkowski, Coord. Chem. Rev., 190-192, 883 (1999); doi:10.1016/S0010-8545(99)00127-7.

M. Beller, B. Cornils, C.D. Frohning and C.W. Kohlpaintner, J. Mol. Catal., 104, 17 (1995); doi:10.1016/1381-1169(95)00130-1.

C.P. Casey, G.T. Whiteker, M.G. Melville, L.M. Petrovich, J.A. Gavney and D.R. Powell, J. Am. Chem. Soc., 114, 5535 (1992); doi:10.1021/ja00040a008.

M. Kranenburg, Y.E.M. Van der Burgt, P.C.J. Kamer, P.W.N.M. Van Leeuwen, K. Goubitz and J. Fraanje, Organometallics, 14, 3081 (1995); doi:10.1021/om00006a057.

H. Klein, R. Jackstell, K.-D. Wiese, C. Borgmann and M. Beller, Angew. Chem. Int. Ed., 40, 3408 (2001); doi:10.1002/1521-3773(20010917)40:18<3408::AID-ANIE3408>3.0.CO;2-A.

J.I. van der Vlugt, R. Sablong, P.C.M.M. Magusin, A.M. Mills, A.L. Spek and D. Vogt, Organometallics, 23, 3177 (2004); doi:10.1021/om0498899.

B. Hamers, E. Kosciusko-Morizet, C. Müller and D. Vogt, Chem. Cat. Chem., 1, 103 (2009); doi:10.1002/cctc.200900088.

O. Diebolt, H. Tricas, Z. Freixa and P.W.N.M. Van Leeuwen, ACS Catal., 3, 128 (2013); doi:10.1021/cs300470u.

S.C. Van der Slot, J. Duran, J. Luten, P.C.J. Kamer and P.W.N.M. van Leeuwen, Organometallics, 21, 3873 (2002); doi:10.1021/om010760y.

Y.J. Yan, X.W. Zhang and X.M. Zhang, J. Am. Chem. Soc., 128, 16058 (2006); doi:10.1021/ja0622249.

R. Jackstell, H. Klein, M. Beller, K.D. Wiese and D. Röttger, Eur. J. Org. Chem., 2001, 3871 (2001); doi:10.1002/1099-0690(200110)2001:20<3871::AID-EJOC3871>3.0.CO;2-V.

L. Zhang, C. Li, X.L. Zheng, H.Y. Fu, H. Chen and R.X. Li, Catal. Lett., 144, 1074 (2014); doi:10.1007/s10562-014-1250-4.

a) J.A. McCleverty, G. Wilkinson, L.G. Lipson, M.L. Maddox and H.D. Kaesz, Inorg. Synth., 8, 211(1966); doi:10.1002/9780470132395.ch56; (b) F. Bonati and G. Wilkinson, J. Chem. Soc., 3156 (1964); doi:10.1039/jr9640003156.

(a) J.F. Barry, T.W. Wallace and N.D.A. Walshe, Tetrahedron Lett., 34, 5329 (1993); doi:10.1016/S0040-4039(00)73988-8; (b) J.F. Barry, T.W. Wallace and N.D.A. Walshe, Tetrahedron, 51, 12797 (1995); doi:10.1016/0040-4020(95)00735-Q.

C.A. Merlic, Y. You, D.M. McInnes, A.L. Zechman, M.M. Miller and Q.L. Deng, Tetrahedron, 57, 5199 (2001); doi:10.1016/S0040-4020(01)00360-X.

C.P. Casey and L.M. Petrovich, J. Am. Chem. Soc., 117, 6007 (1995); doi:10.1021/ja00127a014.

L.A. Van der Veen, M.D.K. Boele, F.R. Bregman, P.C.J. Kamer, P.W.N.M. van Leeuwen, K. Goubitz, J. Fraanje, H. Schenk and C. Bo, J. Am. Chem. Soc., 120, 11616 (1998); doi:10.1021/ja981969e.

F. Shibahara, K. Nozaki and T. Hiyama, J. Am. Chem. Soc., 125, 8555 (2003); doi:10.1021/ja034447u.

E. Zuidema, E. Daura-Oller, J.J. Carbo, C. Bo and P.W.N.M. Van Leeuwen, Organometallics, 26, 2234 (2007); doi:10.1021/om060981+.

Issue

Vol. 27 No. 4 (2015): Vol 27 Issue 4

Synthesis of New N-Pyrrolylphosphane and Its Application in Hydroformylation of 1-Octene

Corresponding Author(s) : H. Chen

Abstract

Keywords

Full Article

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