Highly regioselective hydroaminomethylation of terminal olefins to linear amines using rh complexes with a tetrabi phosphorus ligand

Chemistry - A European Journal

Volumn 17, Issue 51, 2011, Pages 14559-14563

  Liu, Guodu ^a,b   Huang, Kexuan ^b   Cai, Chaoxian ^b   Cao, Bonan ^b   Chang, Mingxin ^b   Wu, Wenjun ^a   Zhang, Xumu ^b  

^a NORTHWEST A F UNIVERSITY   (China)

^b RUTGERS UNIVERSITY   (United States)

Author keywords

hydroaminomethylation; linear amines; olefins; regioselectivity; rhodium; Tetrabi ligand

Indexed keywords

CHEMO-SELECTIVITY; HYDROAMINOMETHYLATION; PHOSPHORUS LIGANDS; PRECURSOR RATIOS; PRODUCT RATIOS; REGIO-SELECTIVE; RH COMPLEXES; SECONDARY AMINES; TERMINAL OLEFINS; TETRAKIS; TURNOVER NUMBER;

AMINES; LIGANDS; OLEFINS; PHOSPHORUS; REGIOSELECTIVITY; RHODIUM;

RHODIUM COMPOUNDS;

ALKENE; AMINE; BIPHENYL DERIVATIVE; LIGAND; ORGANOMETALLIC COMPOUND; ORGANOPHOSPHORUS COMPOUND; RHODIUM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ALKENES; AMINES; BIPHENYL COMPOUNDS; CATALYSIS; LIGANDS; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; ORGANOPHOSPHORUS COMPOUNDS; RHODIUM; STEREOISOMERISM;

EID: 83755207655     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201103073     Document Type: Article

References (26)

1. J. March, Advanced Organic Chemistry, 4 th ed., Wiley, New York, 1992, pp. 768
2. T. E. Müller, M. Beller, Chem. Rev. 1998, 98, 675-703
3. Y. Yamamoto, U. Radhakrishnan, Chem. Soc. Rev. 1999, 28, 199-207.
4. P. Eilbracht, Chem. Rev. 1999, 99, 3329.
5. W. Reppe, Experientia 1949, 5, 93
6. W. Reppe, H. Vetter, Justus Liebigs Ann. Chem. 1953, 582, 133-163.
7. P. Eilbracht, C. L. Kranemann, L. Barfacker, Eur. J. Org. Chem. 1999, 1907-1914
8. T. Rische, L. Barfacker, P. Eilbracht, Eur. J. Org. Chem. 1999, 653-660
9. F. Koc, M. Wyszogrodzka, P. Eilbracht, R. Haag, J. Org. Chem. 2005, 70, 2021-2025.
10. A. Seayad, M. Ahmed, H. Klein, R. Jackstell, T. Gross, M. Beller, Science 2002, 297, 1676-1678
11. M. Ahmed, A. M. Seayad, R. Jackstell, M. Beller, Angew. Chem. 2003, 115, 5773-5777
12. Angew. Chem. Int. Ed. 2003, 42, 5615-5619
13. M. Ahmed, R. P. J. Bronger, R. Jackstell, P. C. J. Kamer, P. W. N. M. van Leeuwen, M. Beller, Chem. Eur. J. 2006, 12, 8979-8988.
14. M. Ahmed, A. M. Seayad, R. Jackstell, M. Beller, J. Am. Chem. Soc. 2003, 125, 10311-10318.
15. Y. Yan, X. Zhang, X. Zhang, J. Am. Chem. Soc. 2006, 128, 16058-16061
16. Y. Yan, X. Zhang, X. Zhang, Adv. Synth. Catal. 2007, 349, 1582-1586
17. S. Yu, Y. Chie, Z. Guan, X. Zhang, Org. Lett. 2008, 10, 3469-3472
18. S. Yu, X. Zhang, Y. Yan, C. Cai, L. Dai, X. Zhang, Chem. Eur. J. 2010, 16, 4938-4943.
19. M. Kranenburg, Y. E. M. van der Burgt, P. C. J. Kamer, P. W. N. M. van Leeuwen, Organometallics 1995, 14, 3081-3089
20. L. A. Van der Veen, M. D. Boele, F. R. Bregman, P. C. Paul, P. W. N. M. van Leeuwen, K. Goubitz, J. Fraanje, H. Schenk, C. Bo, J. Am. Chem. Soc. 1998, 120, 11616-11626
21. J. J. Carbõ, F. Maseras, C. Bo, P. W. N. M. van Leeuwen, J. Am. Chem. Soc. 2001, 123, 7630-7037.
22. C. P. Casey, G. T. Whiteker, M. G. Melville, L. M. Lori, J. A. Gavney, D. R. Powell, J. Am. Chem. Soc. 1992, 114, 5535-5543
23. C. P. Casey, E. L. Paulsen, E. W. Beuttenmueller, B. R. Proft, L. M. Petrovich, B. A. Matter, D. R. Powell, J. Am. Chem. Soc. 1997, 119, 11817-11825.
24. J.-C. Hierso, M. Beauperin, P. Meunier, Eur. J. Inorg. Chem. 2007, 3767-3780
25. D. Evrard, D. Lucas, Y. Mugnier, P. Meunier, J. C. Hierso, Organometallics 2008, 27, 2643-2653.
26. S. Yu, Y. Chie, Z. Guan, Y. Zou, W. Li, X. Zhang, Org. Lett. 2009, 11, 241-244.