High-load, hybrid Si-ROMP reagents

Organic Letters

Volumn 13, Issue 1, 2011, Pages 4-7

  Rolfe, Alan ^a   Loh, Joanna K ^a   Maity, Pradip K ^a   Hanson, Paul R ^a  

^a UNIVERSITY OF KANSAS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

SILICON DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; SCANNING ELECTRON MICROSCOPY;

MICROSCOPY, ELECTRON, SCANNING; MOLECULAR STRUCTURE; SILICON COMPOUNDS;

EID: 78650871524     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol102239h     Document Type: Article

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46. 2Ru=CHPh; cat- B ], and the Hoveyda-Grubbs second-generation catalyst. In all cases studied, cat- B was ideal in both thermal stability and initiation rate.
47. 50 denotes the inorganic surface [Si], followed by the ROMP-derived oligomer grafted [OBAC], followed by the theoretical number of Nb monomer units grafted.
48. We have previously found that there is a good correlation between the mol % of Grubbs catalyst added and the Gaussian distribution of oligomers formed, which is the case with several other oligomers formed [see ref 5d ]. We have made these reagents several times with good reproducibility and consistency. MALDITOF and GPC data are normally attained on all oligomers; however, both methods have failed to give good results for previously published reactive oligomers.
49. 2O.
50. OBAC load stated as mmol/g of acid chloride (ROCl) and further details are reported in ref 17. For load calculation, see Supporting Information S4.
51. www.biotage.com, www.silicycle.com, and www.fluorous.com (accessed June 2010).
52. In comparison to their soluble variants (OBAC, ref 17 and ODCT ref 14b) under identical conditions, no difference in reaction stoichiometry and kinetics was observed. Currently there is no commercially available silica immobilized bis-acid chloride variant for direct comparison, however, Si-ROMP reagents reported within this manuscript produced similar conversions/yields under identical conditions to their soluble variants (OBAC and ODCT).
53. For comparison to reported uses of silica-immobilized dichlorotriazine, see: Kowalski, J. A.; Leonard, S. F.; Lee, G. E., Jr. J. Comb. Chem 2006, 8, 774-779