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Author: Subject: Couple a hydroboration with more than one reaction

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Registered: 25-11-2011
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[*] posted on 19-12-2011 at 12:08
Couple a hydroboration with more than one reaction

Lets say you need to convert an alkene into an anti-Markovnikov type product but instead of attaching one functional group to the less substituted alkenyl carbon, you need to attach 2. So lets say your reagent is isobutylene:

and you want to convert it into 2-chloro-3-methylbutane:

or 1-chloroisobutan-1-ol:

how would you do it? I recently learned about hydroborations and how the organoborane can be converted into other functional groups such as hydroxy, amino and halide groups. Is there a way to attach another substituent to the carbon before replacing the boron group with the other substituent? For example if I wanted to synthesise the first product I mentioned, would there be a way to exploit the unusual situation of the carbon having a boron atom attached to it and somehow attach a methyl group to the carbon before performing the chlorination reaction? Or if I was after the 2nd product, could I somehow chlorinate the atom before performing the oxidation part of the hydroboration-oxidation reaction? Maybe there are better reactions that hydroborations for this kinda thing so if you know of any different anti-Markovnikov electrophilic additions that could be used to do this can you inform me about them. I just want to know how to attach more than one substituent to the less substituted carbon of an alkene.

[Edited on 19-12-2011 by JibbyDee]
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