Recently, I was looking at the chapter on chemoselectivity in Clayden et al.'s Organic Chemistry (2nd ed.). On p. 530, it is mentioned that sodium borohydride reduction only occurs in protic solvents or in the presence of electrophilic metal ions, such as $\ce {Li+}$ and $\ce {Mg^2+}$ while the more powerful reducing agent lithium aluminium hydride does not require protic solvents. Why is that the case?


Clayden, J., Greeves, N., & Warren, S. (2012). Organic Chemistry (2nd ed.). New York : Oxford University Press Inc.

  • 8
    $\begingroup$ Principally solubility. Sodium borohydride is essentially insoluble in aprotic solvents. $\endgroup$
    – Waylander
    Aug 10 '18 at 17:51
  • $\begingroup$ @Waylander What about the need for the ions? These ions help to increase polarity of solvent, increasing the solubility of NaBH4? $\endgroup$ Aug 11 '18 at 1:28
  • 3
    $\begingroup$ Li and Mg cations act as Lewis acids coordinating to carbonyl oxygen, Na is much weaker in this respect. $\endgroup$
    – Mithoron
    Aug 11 '18 at 17:54

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