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Boron-boron multiple bonds are rare, but can be stabilized by NHC adducts. One example is the diborene (RHB=BHR): [20] [21] Each boron atom has an attached proton and is coordinated to a NHC carbene. The parent structure with the additional carbene ligands is diborane(2). [22] [23] A reported diboryne is based on similar chemistry. [24]
The [BAr F 4] − anion with four fluorinated aryl groups distributed tetrahedrally about a central boron atom. Tetrakis[3,5-bis(trifluoromethyl)phenyl]borate is an anion with chemical formula [{3,5-(CF 3) 2 C 6 H 3} 4 B] −, which is commonly abbreviated as [BAr F 4] −, indicating the presence of fluorinated aryl (Ar F) groups.
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 ...
Aromatic C–H borylation was developed by John F. Hartwig and Ishiyama using the diboron reagent Bis(pinacolato)diboron catalyzed by 4,4’-di-tert-butylbipyridine (dtbpy) and [Ir(COD)(OMe)] 2. [15] With this catalyst system the borylation of aromatic C–H bonds occurs with regioselectivity that is controlled by steric effects of the starting ...
Thexylborane [Me 2 CHCMe 2 BH 2] 2 (Me = methyl) is a rare, easily accessed monoalkylborane. One example of a monoalkylborane is thexylborane (ThxBH 2), produced by the hydroboration of tetramethylethylene: [14] B 2 H 6 + 2 Me 2 C=CMe 2 → [Me 2 CHCMe 2 BH 2] 2. A chiral example is monoisopinocampheylborane. Although often written as IpcBH 2 ...
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.
Alpine borane is the commercial name for an organoboron compound that is used in organic synthesis. It is a colorless liquid, although it is usually encountered as a solution. A range of alkyl-substituted borane are specialty reagents in organic synthesis. Two such reagents that are closely related to Alpine borane are 9-BBN and ...
It is a useful reagent in organic synthesis, as a precursor to boronic acids, which are used in Suzuki couplings. These boronic acids are prepared via reaction of the trimethyl borate with Grignard reagents followed by hydrolysis:. [3] [4] ArMgBr + B(OCH 3) 3 → MgBrOCH 3 + ArB(OCH 3) 2 ArB(OCH 3) 2 + 2 H 2 O → ArB(OH) 2 + 2 HOCH 3