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Regioselective C-H Borylation
Silica-SMAP, Silica-TRIP
Pinacol borylation using Halogen-free substrates


These products are catalysts comprising silica gel-supported SMAP and TRIP, compact caged phosphines containing a silicon cross-linking site. Being immobilized on silica gel, two phosphorus atoms (P) form M/P 1:1 complexes without coordinating simultaneously to a single metal atom (M). As a result, a large space can be created around the metal atom, and thereby high activity and broad substrate acceptance can be expected.




1. Features



Features
  • Caged phosphines allow catalysts to be stable in the air.
  • High activity is achieved through immobilization on silica gel.
  • Regioselective C-H borylation is possible.

2. Reactions



2-1. Silica-SMAP (Silica-supported Silicon-constrained Monodentate Trialkylphosphine)
The phosphine moiety is similar in structure to Me3P, and thus shows a high electron-donating ability.

  1) Ortho-selective aromatic C-H borylation with the Ir-Silica-SMAP catalyst

image

  2) CH borynation of quinoline with the Ir-Silica-SMAP catalyst

image

  3) Ortho-borylation of an N-functional aromatic compound with an Rh catalyst

image

  4) o-Borylation of Functionalized Arenes

image


2-2. Silica-TRIP (Silica-Supported Triptycene-Type Phosphine)
The phosphine moiety is similar to PPh3 in steric and electronic properties.

  1) Direct C-H borylation of an alkyl group adjacent to a nitrogen atom

image


3. References



  1. Ochida, A., Hara, K., Ito, H. and Sawamura, M.: Org. Lett., 5, 2671 (2003)
  2. Kawamorita, S., Miyazaki, T., Ohmiya, H., Iwai, T. and Sawamura, M.: J. Am. Chem. Soc., 133, 19310 (2011).
  3. Kawamorita, S., Ohmiya, H., Hara, K., Fukuoka, A. and Sawamura, M.: J. Am. Chem. Soc., 131, 5058 (2009).



4. Product List


Product Name Pkg. Size Wako Catalog No. Grade Storage Condition
Silica-SMAP
1 g
Organic Synthesis
Keep at room temperature
5 g
Silica-TRIP
1 g
5 g

5. Related Products



[Ir(OMe)(cod)]2

D-μ-methoxobis(1,5-cyclooctadiene)diiridium(I)



[12148-71-9]
Keep at 2-10°C.

048-31831
250 mg
044-31833
1 g
042-31834
5 g
 

pinB-Bpin

Bis(pinacolato)diboron



[73183-34-3]
327-56971
1 g
323-56973
5 g
325-56972
25 g
321-56974
100 g
329-56975
250 g
 






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