Also known as DBU. Bicyclic amidine commonly used as a reagent in synthetic organic chemistry. Amidine base used in dehydrohalogenation of halogenated Diels-Alder adducts,1 and in the debromination of 4- or 5-substituted N-benzyl α-bromo-α-p-toluene-sulfonylglutarimide.2 A novel and active catalyst in promoting the methylation reaction of phenols, indoles, and benzimidazoles with dimethyl carbonate under mild conditions,3 catalyst for carboxylic acid esterification with dimethyl carbonate,4 and catalyst for cyclization of 2-alkynylanilines for the metal-free synthesis of indole derivatives.5 Used as a bidentate ligand for atom transfer radical polymerization of (meth)acrylates and styrene.6 The combination with n-perfluorobutanesulfonyl fluoride proves to be a highly efficient system for the conversion of vicinal diols into epoxides.7 Also applied in a new synthesis of the ABCD ring system of Camptothecin.8
References:
1. Tetrahedron 2004, 60, 4821.
2. J. Chin. Chem. Soc. 2002, 49, 1015.
3. Org. Lett. 2001, 3, 4279.
4. J. Org. Chem. 2002, 67, 2188.
5. Adv. Synth. Catal. 2010, 352, 2127.
6. Eur. Poly. J. 2005, 41, 1576.
7. Tetrahedron Lett. 1996, 37, 7497.
8. Org. Lett. 2006, 8, 4665.