An efficient carbonylating reagent. A safer substitute for phosgene. Used in the conversion of several amino acids to the corresponding N-carboxyanhydrides,1 synthesis of 3-aryl-1,3-benzoxazine-2,4-diones from anacardic acids,2 preparation of Weinreb amides from carboxylic acids,3 synthesis of direct dyes containing the ureylene group,4 synthesis of quinazolinedione,5 synthesis of azetidin-2-ones,6 debenzylation of tertiary amines,7 and for liquid and solid-phase aza-peptide synthesis.8
1. Tetrahedron Lett. 1988, 29, 5859.
2. Heterocycles 2005, 65, 311.
3. Lett. Org. Chem. 2007, 4, 20.
4. Dyes Pigm. 1996, 32, 193.
5. Synth. Commun. 1991, 21, 285.
6. Tetrahedron 2002, 58, 2215.
7. J. Org. Chem. 2003, 68, 7289.
8. J. Pept. Sci. 1997, 3, 429.