Triazabicyclodecene:  A Simple Bifunctional Organocatalyst for Acyl Transfer and Ring-Opening Polymerization of Cyclic Esters

Abstract

1,5,7-Triazabicyclo[4.4.0]dec-5-ene (TBD) is an effective organocatalyst for acyl transfer as well as the ring-opening polymerization of cyclic esters. Its high activity is attributed to its ability to simultaneously activate both esters and alcohols, as demonstrated in a model reaction. This unique mechanism makes TBD a remarkably simple example of a bifunctional catalyst. The simplicity of the reaction conditions, the ready commercial availability of the catalyst, and its high activity provide an accessible methodology to allow future studies of tailor-made polyesters.

Amphiphilic block copolymers from a renewable ε-decalactone monomer: prediction and characterization of micellar core effects on drug encapsulation and release

“…The TBD catalyst offered a fast reaction under mild conditions, potentially conferring advantages over Sn(Oct)2 which has been extensively used in ROP previously. [43][44][45] The DSC data demonstrated that the alkyl side chains of ε-DL disrupted the packing in the PεDL block compared to PCL blocks, generating mPEG-b-PεDL micelles with amorphous cores. The finding that PεDL homopolymer was amorphous was also supported by previous studies.…”

Organocatalysis: Fundamentals and Comparisons to Metal and Enzyme Catalysis

“…In an analogous way to benzoic acid that is a bifunctional catalyst (OH: acid; C=O: base), triazabicyclo [4.4.0]dec-5-ene (TBD) is an efficient catalyst of the ring-opening polymerization of cyclic esters (lactones) [59]. The mechanism of the ring-opening reaction of L-lactide [60] and δ-valerolactone [61] (Scheme 4) has been studied computationally.…”

A straightforward synthesis of well‐defined difluorophosphonylated terminated poly(ε‐caprolactone) for grafting onto iron oxide magnetic nanoparticles

“…TBD was chosen for its ability to polymerize cyclic monomers possessing low ring-strain energies such as CL and its efficiency to control the polymerization of CL. 21,26 Experimental conditions to target pCF 2 -functionalized PCLs and characteristics of the resulting polymers are summarized in Table 1 -OCH(CH3)2 5 2 at 4.83 ppm) were used to determine the PCL number-average degree of polymerization (DP n ) equal to 27 (Fig. 1).…”