Continuous Reductions and Reductive Aminations Using Solid Sodium borohydride

• Kerry Gilmore^†
• Stella Vukelic^‡
• D. Tyler McQuade^†§
• Beate Koksch^‡
• Peter H. Seeberger^*†‡

• ^† Max Planck Institute of Colloids and Interfaces, Germany
• ^‡ Institute of Chemistry and Biochemistry, Freie Universität Berlin, Germany
• ^§ Department of Chemistry and Biochemistry, Florida State University, United States

Most successful reactions carried out under continuous flow conditions mix homogeneous solutions yielding homogeneous products. Using solids is avoided to prevent pump and reactor clogging; even though solid reagents may often be the best choice for a given transformation. Here we demonstrate that by pumping aldehydes, ketones, or in situ formed imines through a specially formulated NaBH4 column results in efficient reductions. The column design and performance characteristics, along with substrate scope, are discussed.

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