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This chemical reaction is useful in the organic synthesis of organic compounds. [1] Hydroboration produces organoborane compounds that react with a variety of reagents to produce useful compounds, such as alcohols, amines, or alkyl halides. The most widely known reaction of the organoboranes is oxidation to produce alcohols from alkenes.
Boron-boron multiple bonds are rare, although doubly-bonded dianions have been known since the 1990s. [20] Neutral analogues use NHC adducts, such as the following diborane(2) derivative: [21] [22] Each boron atom has an attached proton and is coordinated to a NHC carbene. [23] [24] A reported diboryne is based on similar chemistry. [25]
The boron reagent is converted to boric acid. The reaction was originally described by H.C. Brown in 1957 for the conversion of 1-hexene into 1-hexanol. [3] Hexanol synthesis. Knowing that the group containing the boron will be replaced by a hydroxyl group, it can be seen that the initial hydroboration step determines the regioselectivity.
In the US, a team led by Schlesinger developed the basic chemistry of the anionic boron hydrides and the related aluminium hydrides. Schlesinger's work laid the foundation for a host of boron hydride reagents for organic synthesis, most of which were developed by his student Herbert C. Brown. Borane-based reagents are now widely used in organic ...
Diisopinocampheylborane is an organoborane that is useful for asymmetric synthesis. This colourless solid is the precursor to a range of related reagents. The compound was reported in 1961 by Zweifel and Brown in a pioneering demonstration of asymmetric synthesis using boranes. The reagent is mainly used for the synthesis of chiral secondary ...
Organoboron compounds have broad applications for chemical synthesis because the C–B bond can easily be converted into a C–X (X = Br, Cl), C–O, C–N, or C–C bond. Because of the versatility of the C–B bond numerous processes have been developed to incorporate them into organic compounds. [ 7 ]
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.
Dibutylboron trifluoromethanesulfonate (also called dibutylboron triflate or DBBT) is a reagent in organic chemistry. Its chemical formula is C 9 H 18 BF 3 O 3 S. It is used in asymmetric synthesis for example in the formation of boron enolates in the aldol reaction. [1]