Borohydride reaction is one of the important organic synthesis reactions.Ethane boraneMethylborane dissociated in ether solution is added with unsaturated bond of alkene and alkyne by B-H bond to form organic boron compound.Its characteristics are: (1) No rearrangement occurs in the reaction process;(2) The reaction is cis addition;(3) The addition with asymmetric olefins conforms to the anti Markov Nikov rule.
Borohydride reaction is one of the important organic synthesis reactions.Created by Herbert Charles Brown.Ethane boraneMethylborane dissociated in ether solution is added with unsaturated bond of alkene and alkyne by B-H bond to form organic boron compound.
Reaction characteristics
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(1) No rearrangement occurs in the reaction process;
(2) The reaction is cis addition;
(3) The addition with asymmetric olefins conforms to the anti Markov Nikov rule.The boron atom is added to the double bond carbon atom with more hydrogen atoms, while the hydrogen is added to the carbon atom with less hydrogen atoms.
Reaction type
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Organoborane is a multifunctional intermediate, which can be used to synthesize various types of organic compounds.For example, the borohydride oxidation reaction of olefins can produce alcohols;Alkynes can be hydroborated and oxidized to produce aldehydes and ketones.It should be noted that ethane is a gas that can spontaneously ignite in air and cannot be prepared in advance. Usually, the ether solution of boron fluoride is added to the mixture of sodium borohydride and olefins to make ethane react with olefins once it is established.Commercial borane is a tetrahydrofuran solution of borane.
Common reagents
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9-boron bicyclic [3.3.1] nonane (dimer) (also known as 9-BBN DIMER) can be used as borohydride reaction reagent, which has high selectivity in reaction with olefins. When controlling conditions, it can only react with double bonds with small steric hindrance.The generated alkyl boron can carry out a variety of reactions, and is widely used in the formation of hydrocarbon bond, carbon oxygen bond, carbon nitrogen bond, carbon carbon bond, such as oxidation to alcohol, reduction to hydrocarbon, and Suzuki reaction.It is widely used in organic synthesis.[1]
