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Reduction of conjugated double bond by sodium borohydride

Brian Day  Follow

Scifinder shows lots of reactions such as you describe. Often (but not always) copper is used to help favour the 1,4-addition (alkene reduction) process.

scifinder screenshot

The simplest example I can see is the reduction of 3-penten-2-one[[2]] - when treated with NaBH4 the majority (89%) is reduced at the ketone only, while 11% of the doubly-reduced product is formed:

enone reduction

Obviously different substrates would give different product ratios, but certainly this is a plausible (and precedented) reaction.

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Jhans Zimner  Follow
Thanks a lot. But why does it have such a low yield in the example you gave. I dont see much steric hindrance. Do you know the reason?More
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Gevorg Ter-Isahakyan  Follow
Related question: More
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Edmnjds56-  Follow
As a rule, NaBH4 reduces 1,2.More
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James Conlon  Follow
chemistry.stackexchange.com/questions/87138/…More
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