Triazabicyclodecene (1,5,7-triazabicyclo[4.4.0]dec-5-ene or TBD) is a commercially available bicyclic strong guanidine base (pKa = 25.98 in CH3CN and pKa = 21.00 in THF). TBD is an organic soluble base that has been used effectively for a variety of base-mediated organic transformations such as:
Michael reactions,Henry (nitroaldol reactions),Wittig reactions,Horner–Wadsworth–Emmons reactions,transesterification reactions,etherifications,ring-opening polymerizations (Scheme 1),tautomerizations and epimerizationsP–C and P–N bond formations,Knoevenagel condensations,deprotonation reactions of phenols, carboxylic acids and C-acids (Scheme 2),aminolysis of esters.It is also known in deprotonated form (at the 7-position), often as a ligand, for instance in Ditungsten tetra(hpp)
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