3 years ago

Tris(2,4,6-trifluorophenyl)borane: An Efficient Hydroboration Catalyst

Tris(2,4,6-trifluorophenyl)borane: An Efficient Hydroboration Catalyst
Rebecca L. Melen, Lewis C. Wilkins, James R. Lawson
The metal-free catalyst tris(2,4,6-trifluorophenyl)borane has demonstrated its extensive applications in the 1,2-hydroboration of numerous unsaturated reagents, namely alkynes, aldehydes and imines, consisting of a wide array of electron-withdrawing and donating functionalities. A range of over 50 borylated products are reported, with many reactions proceeding with low catalyst loading under ambient conditions. These pinacol boronate esters, in the case of aldehydes and imines, can be readily hydrolyzed to leave the respective alcohol and amine, whereas alkynyl substrates result in vinyl boranes. This is of great synthetic use to the organic chemist. What a boron discovery: The use of tris(2,4,6-trifluorophenyl)borane in the metal-free 1,2-syn-hydroboration of various unsaturated moieties such as alkynes, aldehydes and imines generates a plethora of over 50 borylated products with many reactions proceeding with low catalyst loading under ambient conditions.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/chem.201703109

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