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hydroboration
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hydroboration
hydroboration Chem. (ˌhaɪdrəʊbɔəˈreɪʃən) [f. hydro- + boron + -ation.] The addition of a linked boron–hydrogen pair of atoms in a molecule across a double or triple bond between a carbon atom and another atom; for example, {b2}B{b1}H + C{btc1}{bbc1}{b2}C{btc1}{bbc1} → {b2}B{b1}C{btc1}{bbc1}{b1}C{btc...
Oxford English Dictionary
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Hydroboration
Another research subtheme is metal-catalysed hydroboration. See also
Hydroboration–oxidation reaction
References
Organic reactions
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Hydroboration-oxidation: Mechanism (video) | Khan Academy
The Na⁺ ions are simply spectator ions during the whole process. Their function is to balance the charge of the negative ions. The NaOH serves two main functions: 1. It converts the hydrogen peroxide into a more nucleophilic hydroperoxide ion. HO⁻ + HOOH → HOH + ⁻OOH.
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Base-free nickel-catalyzed hydroboration of simple alkenes ...
by JF Li · 2017 · Cited by 51 — Base-free nickel-catalyzed hydroboration of simple alkenes with bis(pinacolato)diboron in an alcoholic solvent†. Check for updates. Jiang-Fei Li,ab Zhen-Zhong ...
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Hydroboration–oxidation reaction
Hydroboration proceeds in an anti-Markovnikov manner. Alkyne hydroboration
A hydroboration reaction also takes place on alkynes.
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hydroborate
▪ I. hydroborate, n. Chem. (haɪdrəʊˈbɔəreɪt) [f. hydro- + borate.] = borohydride.1950 Chem. Abstr. XLIV. 12392/1 (Index), Hydroborates. See such headings as Aluminium borohydride and Lithium borohydride. 1963 Jrnl. Amer. Chem. Soc. LXXXV. 2725/1 Among the numerous derivatives of boranes and hydrobor...
Oxford English Dictionary
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Metal-catalysed hydroboration
These two borane compounds are otherwise slow to participate in hydroboration. Catalyzed hydroboration-oxidation of substituted alkenes can be rendered enantioselective.
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Hydrometalation
Examples are hydroboration, hydroalumination, hydrosilylation and hydrozirconation.
References
Organometallic chemistry
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Hydrofunctionalization
Examples
Some of the better known classes of hydrofunctionalization reactions include the following:
Hydroboration
Hydrosilylation
Hydrometalation (including
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3-Hexanol
Reactions
3-Hexanol can be synthesized by the hydroboration of unsaturated hexane compounds such as 3-hexyne.
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9-Borabicyclo(3.3.1)nonane
This colourless solid is used in organic chemistry as a hydroboration reagent.
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3-Hydroxytetrahydrofuran
in 95.8% optical purity from L-malic acid via an esterification-reduction-cyclodehydration sequence. 3-hydroxytetrahydrofuran has been synthesized via hydroboration of 2,3- and 2,5-dihydrofuran employing various borane reagents and chiral 3-hydroxytetrahydrofurans have also been prepared by catalytic asymmetric hydroboration
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Borane
Borane adducts are widely used in organic synthesis for hydroboration, where BH3 adds across the C=C bond in alkenes to give trialkylboranes:
(THF)BH3 Hydroboration can be coupled with oxidation to give the hydroboration-oxidation reaction.
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Disiamylborane
It is used for hydroboration–oxidation reactions of terminal alkynes, giving aldehydes via anti-Markovnikov hydration followed by tautomerization. Thexylborane ((1,1,2-trimethylpropyl)borane, ThxBH2), a primary borane obtained by hydroboration of tetramethylethylene.
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Tuataric acid
Tuataric acid can be prepared from pent-4-yn-1-ol through a sequence that begins with the extension of the alkyne terminus by hydroboration and ends with
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