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Hydroboration
In organic chemistry, hydroboration refers to the addition of a hydrogen-boron bond to certain double and triple bonds involving carbon (C=C, C=N, C=O, and C≡C). This chemical reaction is useful in the organic synthesis of organic compounds.
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.
The development of this technology and the underlying concepts were recognized by the Nobel Prize in Chemistry to Herbert C. Brown.
Much of the original work on hydroboration employed diborane as a source of BH3. Usually however, borane dimethylsulfide complex BH3S(CH3)2 (BMS) is used instead. It can be obtained in highly concentrated forms.
The adduct BH3(THF) is also commercially available as THF solutions. Its shelf life is less than BMS.
In terms of synthetic results, diborane or the more conveniently handle BMS and borane-THF are equivalent.
The stoichiometry and idealized regiochemistry of hydroboration of terminal alkenes follows:
In reality, each hydroboration step follows 1,2-addition but ca. 4% gives the 2,1 addition (affording the B(CH(CH3)R isomer). In extreme cases, such as risubstituted alkenes, hydroboration affords. This significant rate difference in producing di- and tri-alkyl boranes is useful in the synthesis of bulky boranes that can enhance regioselectivity.
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Hydroboration
In organic chemistry, hydroboration refers to the addition of a hydrogen-boron bond to certain double and triple bonds involving carbon (C=C, C=N, C=O, and C≡C). This chemical reaction is useful in the organic synthesis of organic compounds.
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.
The development of this technology and the underlying concepts were recognized by the Nobel Prize in Chemistry to Herbert C. Brown.
Much of the original work on hydroboration employed diborane as a source of BH3. Usually however, borane dimethylsulfide complex BH3S(CH3)2 (BMS) is used instead. It can be obtained in highly concentrated forms.
The adduct BH3(THF) is also commercially available as THF solutions. Its shelf life is less than BMS.
In terms of synthetic results, diborane or the more conveniently handle BMS and borane-THF are equivalent.
The stoichiometry and idealized regiochemistry of hydroboration of terminal alkenes follows:
In reality, each hydroboration step follows 1,2-addition but ca. 4% gives the 2,1 addition (affording the B(CH(CH3)R isomer). In extreme cases, such as risubstituted alkenes, hydroboration affords. This significant rate difference in producing di- and tri-alkyl boranes is useful in the synthesis of bulky boranes that can enhance regioselectivity.