Cobalt-catalyzed dimerization of α-olefins to give linear α-olefin products

Journal of the American Chemical Society

Volumn 127, Issue 49, 2005, Pages 17194-17195

  Broene, Richard D ^a   Brookhart, Maurice ^b   Lamanna, William M ^c   Volpe Jr , Anthony F ^b,d  

^a BOWDOIN COLLEGE   (United States)

^b The University of North Carolina at Chapel Hill   (United States)

^c 3M COMPANY   (United States)

^d SYMYX TECHNOLOGIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 HEXENE; ALKENE DERIVATIVE; COBALT; DIMER; MONOMER;

ADDITION REACTION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONCENTRATION RESPONSE; DIMERIZATION; ELIMINATION REACTION; ISOMERIZATION; OLIGOMERIZATION; PROTON TRANSPORT; REACTION ANALYSIS; REPRODUCIBILITY; STRUCTURE ANALYSIS; SYNTHESIS; TECHNIQUE;

EID: 29044441233     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja056655n     Document Type: Article

References (18)

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2. For Cr catalysts: (a) Carter, A.; Cohen, S. A.; Cooley, N. A.; Murphy, A.; Scutt, J.; Wass, D. F. Chem. Commun. 2002, 858.
3. (b) McGuinness, D. S.; Wasserscheid, P.; Morgan, D. H.; Dixon, J. T. Organometallics 2005, 24, 552.
4. (c) For Ta catalysis: Andes, C.; Harkins, S. B.; Murtuza, S.; Oyler, K.; Sen, A. J. Am. Chem. Soc. 2001, 123, 7423.
5. (d) For Ti catalysis: Deckers, P. J. W.; Hessen, B.; Teuben, J. H. Angew. Chem., Int. Ed. 2001, 40, 2516.
6. Bollmann, A. et al. J. Am. Chem. Soc. 2004, 126, 14712.
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12. Brookhart, M.; Lincoln, D. M.; Volpe, A. F.; Schmidt, G. F. Organometallics 1989, 8, 1212.
13. Preliminary accounts of this work have appeared in (a) Brookhart, M.; Volpe, A. F.; DeSimone, J. M.; Lamanna, W. M. Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.) 1991, 32, 461.
14. (b) Volpe, A. F., Jr. Olefin Polymerization Catalysts Based on Highly Electrophilic Co(III) Complexes: Mechanistic Studies and Catalyst Design. Ph.D. Thesis, University of North Carolina Chapel Hill, 1991. The structure of dimer C was reported incorrectly in (a).
15. 3 should improve the regioselectivity of the insertion.
16. Different batches of catalyst provide slightly different ratios of A/B/C. For instance, use of the same catalyst batch for the oligomerization as is used for the reaction shown in Figure 2 gives a ratio of 81:6:13.
17. The isomerization of 1-dodecene is assumed to be metal catalyzed, but we have not yet identified the active species. No free HBArF was observed when a deficit was used to promote the reaction.
18. Use of greater than 1 equiv of HBArF gave olefin isomerization to internal olefin products presumably through an acid-catalyzed process.