Strong organic base useful for the formation of organic-soluble salts, and as a basic catalyst, e.g. in Michael addition reactions: J. Org. Chem., 27, 3175 (1962); Tetrahedron Lett., 569 (1973). Preferred catalyst in the Michael addition of aliphatic nitro compounds to unsaturated esters: Synthesis, 44 (1972); 953 (1989); Tetrahedron Lett., 30, 993 (1989). Useful base for formation of TBDMS ethers of alcohols with tert-Butyl-dimethyl-chlorosilane: J. Org. Chem., 49, 4657 (1984). For use in the Baylis-Hillman reaction, see: J. Chem. Soc., Perkin 1, 2831 (2001). Inexpensive and efficient ligand for the palladium-catalyzed Heck reaction: Synlett, 1885 (2005).Other uses include: Acylation of amino acids by methyl trifluoroacetate: Synthesis, 399 (1976). Formation of Boc-amino acids with tert-butyl phenyl carbonate: Org. Synth. Coll., 6, 203 (1988). Cleavage of peptides from resins: Tetrahedron, 40, 4237 (1984). Selective cleavage of a primary benzyloxycarbonyl (Cbz, Z) group in the presence of either Boc or secondary Cbz: J. Chem. Soc., Perkin 1, 1905 (1988).
