Lipshutz DCAD Coupling Reagent

Aldrich ChemFiles 2007, 7.3, 10.

Aldrich ChemFiles 2007, 7.3, 10.

The Mitsunobu reaction is one of the most extensively used coupling reactions in organic synthesis and typically azodicarboxylate reagents such as DEAD or DIAD are employed. However, drawbacks such as low room temperature stability and difficulty in removing hydrazine byproducts detract from the practicability of these reagents. Recent work by Professor Bruce Lipshutz and co-workers details the development of a new azodicarboxylate for the Mitsunobu reaction.1 DCAD is a solid reagent and can easily be stored and handled at room temperature, unlike the more common DEAD and DIAD reagents. DCAD exhibits comparable reactivity to DEAD in common Mitsunobu couplings; however, unlike DEAD, the reduced hydrazine byproduct of DCAD is easily removed by simple precipitation directly from the reaction mixture, and is easily recycled in high yield to regenerate DCAD.

back to top

Materials

     

References

  1. Lipshutz, B. H. et al. Org. Lett. 2006, 8, 5069.

back to top

Related Links