1,8-Diazabicyclo(5.4.0)undec-7-ene explained

1,8-Diazabicyclo[5.4.0]undec-7-ene, or more commonly DBU, is a chemical compound and belongs to the class of amidine compounds. It is used in organic synthesis as a catalyst, a complexing ligand, and a non-nucleophilic base.^[1]

Occurrence

Although all commercially available DBU is produced synthetically, it may also be isolated from the sea sponge Niphates digitalis.^[2] The biosynthesis of DBU has been proposed to begin with adipaldehyde and 1,3-diaminopropane.

Uses

As a reagent in organic chemistry, DBU is used as a ligand and base. As a base, protonation occurs at the imine nitrogen.^[3] Lewis acids also attach to the same nitrogen.^[4]

These properties recommend DBU for use as a catalyst, for example as a curing agent for epoxy resins and polyurethane.

It is used in the separation of fullerenes in conjunction with trimethylbenzene. It reacts with C₇₀ and higher fullerenes, but not with C₆₀.

It is useful for dehydrohalogenations.^[5]

See also

• 1,5-Diazabicyclo[4.3.0]non-5-ene
• DABCO

References

1. 10.1055/s-2004-815436. DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) - A Nucleophillic Base. Synlett. 3. 574–575. 2004. Ghosh. Nandita. free.
2. E. L. Regalado. Judith Mendiola. Abilio Laguna. Clara Nogueiras. Olivier P Thomas. Nat. Prod. Commun.. 2010. 5. Polar alkaloids from the Caribbean marine sponge Niphates digitalis. 8 . 1187–1190 . 20839615.
3. Parviainen . Arno . King . Alistair W. T. . Mutikainen . Ilpo . Hummel . Michael . Selg . Christoph . Hauru . Lauri K. J. . Sixta . Herbert . Kilpeläinen . Ilkka . Predicting Cellulose Solvating Capabilities of Acid–Base Conjugate Ionic Liquids . ChemSusChem . 6 . 11 . 2013 . 1864-5631 . 10.1002/cssc.201300143 . 2161–2169.
4. Romero . Erik A. . Zhao . Tianxiang . Nakano . Ryo . Hu . Xingbang . Wu . Youting . Jazzar . Rodolphe . Bertrand . Guy . Tandem copper hydride–Lewis pair catalysed reduction of carbon dioxide into formate with dihydrogen . Nature Catalysis . 1 . 10 . 2018-10-01 . 2520-1158 . 10.1038/s41929-018-0140-3 . 743–747.
5. Book: 10.1002/047084289X.rd011.pub2 . 1,8-Diazabicyclo[5.4.0]undec-7-ene . Encyclopedia of Reagents for Organic Synthesis . 2006 . Savoca . Ann C. . Urgaonkar . Sameer . 0-471-93623-5 .