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Introduction
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Nitriles can be reduced to primary amines using reducing agents like lithium aluminum hydride or catalytic hydrogenation. The reduction introduces an amino group with an extra carbon in the skeleton. Nitriles are formed from the reaction between alkyl halides and sodium cyanide through the SN2 mechanism. Primary alkyl halides are the preferred substrates to prepare nitriles.
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Continuous-Flow Amide and Ester Reductions Using Neat Borane Dimethylsulfide Complex.

Sándor B Ötvös1, C Oliver Kappe1,2

  • 1Institute of Chemistry, University of Graz, NAWI Graz, Heinrichstrasse 28, 8010, Graz, Austria.

Chemsuschem
|January 3, 2020
PubMed
Summary
This summary is machine-generated.

This study introduces a novel flow chemistry method for reducing amides and esters using borane dimethylsulfide complex (BH₃⋅DMS). This efficient process offers high yields and selectivity, reducing waste and environmental impact compared to traditional batch methods.

Keywords:
amidesboranescontinuous flowestersreduction

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Area of Science:

  • Synthetic Organic Chemistry
  • Green Chemistry
  • Chemical Engineering

Background:

  • Amide and ester reductions are crucial in synthesis, with many established batch protocols.
  • Flow chemistry applications for these reductions, particularly amides, remain underexplored.

Purpose of the Study:

  • To develop a simple, efficient continuous-flow process for amide and ester reductions.
  • To utilize borane dimethylsulfide complex (BH₃⋅DMS) in a solvent-free flow system.
  • To enhance productivity and reduce environmental impact (E-factors).

Main Methods:

  • Employed neat borane dimethylsulfide complex (BH₃⋅DMS) in a continuous-flow reactor.
  • Optimized short residence times for high selectivity and yield.
  • Conducted solvent-free reactions with high substrate concentrations.

Main Results:

  • Achieved high yields and selectivity for alcohol and amine products.
  • Demonstrated outstanding productivity and reduced E-factors due to solvent-free conditions.
  • Successfully synthesized multigram quantities of pharmaceutically relevant compounds.

Conclusions:

  • The developed flow protocol is simple, scalable, and cost-effective.
  • It offers reduced solvent and reagent consumption, aligning with green chemistry principles.
  • Presents a more environmentally benign alternative to traditional batch reductions.