hydroboration
Quick Summary
Hydroboration is a chemical reaction where boron hydrides, such as BH3, are easily added to unsaturated organic compounds like alkenes and alkynes. This process, developed by Herbert C. Brown, leads to the formation of organoboranes. These organoboranes can then be further transformed into other organic compounds, such as alcohols, through oxidation. The hydroboration reaction is significant because it allows for stereospecific synthesis and proceeds with a regioselectivity opposite to the Markovnikov rule. This reaction was a key development in organic synthesis and contributed to Brown sharing the Nobel Prize in Chemistry in 1979.12
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borane…the 1979 prize for his hydroboration reaction (1956), the remarkably easy addition of BH3 (in the form of BH3 · S) to unsaturated organic compounds (i.e., alkenes and alkynes) in ether solvents (S) at room temperature to yield organoboranes quantitatively (that is, in a reaction that proceeds wholly, or almost…
Read More…the 1979 prize for his hydroboration reaction (1956), the remarkably easy addition of BH3 (in the form of BH3 · S) to unsaturated organic compounds (i.e., alkenes and alkynes) in ether solvents (S) at room temperature to yield organoboranes quantitatively (that is, in a reaction that proceeds wholly, or almost…
Read More- boraneReactions and synthesis of boranes
The stereospecific hydroboration reaction mentioned above, 3RCH=CH2 + 1/2B2H6 → B(CH2CH2R)3 (where R is an alkyl group), nearly quantitatively yields organoboranes, which in turn can yield various organic compounds such as the alkane corresponding to the initial alkene or the primary alcohol.
Read MoreThe stereospecific hydroboration reaction mentioned above, 3RCH=CH2 + 1/2B2H6 → B(CH2CH2R)3 (where R is an alkyl group), nearly quantitatively yields organoboranes, which in turn can yield various organic compounds such as the alkane corresponding to the initial alkene or the primary alcohol.
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