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Pinacolborane is used as a precursor of boronic esters by hydroboration or coupling reactions. It acts as a monofunctional hydroborating agent. It is used in the synthesis of unsymmetrical biaryls through aromatic C-H borylation-cross-coupling sequence. It is involved in the preparation of 4,4,5,5-tetramethyl-2-thiophen-2-yl-[1,3,2]dioxaborolane by reacting with 2-iodo-thiophene. Further, it is used to prepare vinylboronates by palladium-catalyzed coupling with alkenyl triflates and iodides.
Precursor of boronic esters by hydroboration or coupling reactions. Hydroboration of alkynes, in the presence of Rh or Ni catalysts, yields alkenylboronates: Tetrahedron Lett., 37, 3283 (1996). Hydroboration of alkenes in the presence of Chlorotris(triphenylphosphine)rhodium(I), 10468 , affords the alkylboronate: Tetrahedron Lett., 37, 3283 (1996); with phosphine-free catalyst Chloro(1,5-cyclooctadiene)rhodium(I) dimer, 10466 , dehydrogenative borylation predominates to give the alkenylboronate: Tetrahedron Lett., 40, 213 (1999); Bull. Chem. Soc. Jpn., 75, 825 (2002):
Coupling aryl iodides and bromides, catalyzed by [1,1'-Bis(diphenylphosphino)ferrocene]palladium(II) chloride, 41225 , gives the aryl pinacolboronates: J. Org. Chem., 62, 6458 (1997); 65, 164 (2000). In the presence of triphenylarsine, Pd-catalyzed coupling with alkenyl triflates and iodides affords vinylboronates: Synthesis, 778 (2000). For a brief review of uses of pinacolborane, see: Synlett, 1210 (2000).
Okada, S.; Namikoshi, T.; Watanabe, S.; Murata, M. Ruthenium-Catalyzed Ortho-Selective Aromatic C-H Borylation of 2-Arylpyridines with Pinacolborane. ChemCatChem. 2015, 7 (10), 1531-1534.
Guo, J.; Chen, J.; Lu, Z. Cobalt-catalyzed asymmetric hydroboration of aryl ketones with pinacolborane. Chem. Commun. 2015, 51 (26), 5725-5727.
Hazard Statements: H225-H261-H333-H319
Highly flammable liquid and vapour. In contact with water releases flammable gas. May be harmful if inhaled. Causes serious eye irritation.
Precautionary Statements: P223-P210-P231+P232-P303+P361+P353-P305+P351+P338-P501a
Keep away from any possible contact with water, because of violent reaction and possible flash fire. Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Handle under inert gas. Protect from moisture. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Dispose of contents/container in accordance with local/regional/national/international regulations.