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Catecholborane is used to prepare B-alkylcatecholboranes. It finds application for the preparation of amides and macrocyclic lactams from carboxylic acids. It is used as a stereoselective reducing agent to convert beta-hydroxy ketones to syn 1,3-diols. Further, it reacts with alkyne through hydroboration to form trans vinyl borane, which is a precursor to Suzuki reaction.
Mild, selective hydroborating agent: J. Am. Chem. Soc., 97, 5249 (1975); Tetrahedron, 32, 981 (1976). Use of Rh(I) and Ir(I) catalysis increases stereo- and regioselectivity: J. Am. Chem. Soc., 114, 6671, 6674 (1992). For Rh catalyzed enantioselective hydroboration of alkenylboronic acids, see: Tetrahedron: Asymmetry, 7, 5 (1996). Hydroboration of olefins can be accomplished at room temperature in the presence of N,N-dimethylacetamide: J. Org. Chem., 61, 3224 (1996).
For a brief feature on uses of this reagent in Organic synthesis, see: Synlett, 666 (2007).
Phothongkam, S.; Uang, B. J. Enantioselective Reduction of Ketones Induced by a C2-Symmetrical Chiral Hydroxyamide/Titanium(IV) complex. Asian J. Org. Chem. 2015, 4 (8), 794-799.
Yang, Y.; Xu, M.; Song, D. Organocatalysts with carbon-centered activity for CO2 reduction with boranes. Chem. Commun. 2015, 51 (56), 11293-11296.
Hazard Statements: H225-H314-H318
Highly flammable liquid and vapour. Causes severe skin burns and eye damage. Causes serious eye damage.
Precautionary Statements: P210-P260u-P303+P361+P353-P305+P351+P338-P405-P501a
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. 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. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.