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Catecholborane - 1 reference result

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Catecholborane

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Catecholborane, or BHcat, is a derivative of catechol and a boron hydride, with the formula C₆H₄O₂BH. It is commonly used in organic syntheses.

Synthesis

Traditionally catecholborane commonly is produced by reacting catechol with borane (BH₃) in a cooled solution of THF. However, this method results in a loss of 2 mole equivalents of the hydride.

Heinrich Noth and Detlef Mannig devised a method that allows a more efficient recovery of the final product, catecholborane, and subsequently a greater yield. Their method involves reacting an alkali-metal boron hydride (LiBH₄, NaBH₄, of KBH₄) with tris(catecholato)bisborane in an ether solvent such as diethyl ether or diethylene glycol.

In 2001 Herbert Brown released an additional procedure for catecholborane synthesis. His method involves reacting tri-O-phenylene bis-borate with diborane in a solution of either triglyme or tetraglyme. Brown claimed his method produces 85% yield of 97% pure product, catecholborane.

Reactions

Preparation of an organoborane

When catecholborane is reacted with an alkyne, usually a terminal alkyne, through hydroboration a trans vinylborane is formed. This is the precursor to the Suzuki reaction.