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Compounds of the type BR n (OR) 3-n are called borinic esters (n = 2), boronic esters (n = 1), and borates (n = 0). Boronic acids are key to the Suzuki reaction. Trimethyl borate, debatably not an organoboron compound, is an intermediate in sodium borohydride production.
A borane is a compound with the formula BR x H y although examples include multi-boron derivatives. A large family of boron hydride clusters is also known. In addition to some applications in organic chemistry , the boranes have attracted much attention as they exhibit structures and bonding that differs strongly from the patterns seen in ...
Industrially, triethylborane is used as an initiator in radical reactions, where it is effective even at low temperatures. [1] As an initiator, it can replace some organotin compounds. It reacts with metal enolates , yielding enoxytriethylborates that can be alkylated at the α-carbon atom of the ketone more selectively than in its absence.
When only one functional group is present borylation occurs in the meta and para position in statistical ratios of 2:1 (meta:para). The ortho isomer is not detected due to the steric effects of the substituent. [16] Meta-para borylation. Addition of Bpin occurs in only one position for symmetrically substituted 1,2- and 1,4-substituted arenes.
Borane dimethylsulfide (BMS) is a complexed borane reagent that is widely used for hydroborations. [4] Much of the original work on hydroboration employed diborane as a source of BH 3. Usually however, borane dimethylsulfide complex BH 3 S(CH 3) 2 (BMS) is used instead. [5] It can be obtained in highly concentrated forms. [6]
Borane makes a strong adduct with triethylamine; using this adduct requires harsher conditions in hydroboration. This can be advantageous for cases such as hydroborating trienes to avoid polymerization. More sterically hindered tertiary and silyl amines can deliver borane to alkenes at room temperature. Borane(5) is the dihydrogen complex of
9-Borabicyclo[3.3.1]nonane or 9-BBN is an organoborane compound. This colourless solid is used in organic chemistry as a hydroboration reagent. The compound exists as a hydride-bridged dimer, which easily cleaves in the presence of reducible substrates. [1] 9-BBN is also known by its nickname 'banana borane'. [2]
Tris(2,2,2-trifluoroethyl) borate can be prepared by reaction of trifluoroethanol with boron trichloride, borane dimethylsulfide, boron tribromide, or boric anhydride.The latter is more convenient for larger scale preparations due to its low cost and ease of handling.