Synlett 2014; 25(6): 894-895
DOI: 10.1055/s-0033-1340852
spotlight
© Georg Thieme Verlag Stuttgart · New York

1,5,7-Triazabicyclo[4.4.0]dec-5-ene (TBD) as a Lewis Base

Aleksej Turočkin
RWTH Aachen University, Institute of Organic Chemistry, ­Landoltweg 1, 52074 Aachen, Germany   Email: aleksej.turockin@rwth-aachen.de
› Author Affiliations
Further Information

Publication History

Publication Date:
14 February 2014 (online)

Introduction

1,5,7-Triazabicyclo[4.4.0]dec-5-ene (TBD, 1) was first synthesized by McKay and Kreling in the laboratories of Monsanto Canada Limited in 1957.[1] This bicyclic guanidine possesses a remarkably high Brønsted basicity (pKa = 28 in MeCN)[2] and has found broad applications as an organic superbase.[3] Moreover, the nucleophilic properties of guanidines have also been studied.[4] Mayr and co-workers quantified the nucleophilicities for a series of guanidines,[5] and TBD was by far the most powerful nucleophile among the investigated structures. In fact, TBD was found to be an even stronger nucleophile than the well-known Lewis base 4-dimethylaminopyridine (DMAP). In order to highlight the synthetic utility and usefulness of TBD as a Lewis base, a short overview of recent applications is presented.

Zoom Image
Figure 1 Commercially available bicyclic guanidine base 1,5,7-tri­a­zabicyclo[4.4.0]dec-5-ene (TBD, 1)
 
  • References

  • 1 McKay AF, Kreling M.-E. Can. J. Chem. 1957; 35: 1438
  • 2 Kaljurand I, Kütt A, Sooväli L, Rodima T, Mäemets V, Leito I, Koppel IA. J. Org. Chem. 2005; 70: 1019
  • 3 Superbases for Organic Synthesis. Ishikawa T. John Wiley and Sons; Chichester: 2009
    • 4a Fu X, Tan C.-H. Chem. Commun. 2011; 47: 8210
    • 4b Taylor JE, Bull SD, Williams JM. J. Chem. Soc. Rev. 2012; 41: 2109
  • 5 Maji B, Stephenson DS, Mayr H. ChemCatChem 2012; 4: 993
  • 6 For the crystallographic characterization of TBD-CO2 carbamate, see: Villiers C, Dognon J.-P, Pollet R, Tuéry P, Ephritikhine M. Angew. Chem. Int. Ed. 2010; 49: 3465
  • 7 Wang X, Lim YN, Lee C, Jang H.-Y, Lee BY. Eur. J. Org. Chem. 2013; 1867
  • 8 Huang S, Ma J, Li J, Zhao N, Wei W, Sun Y. Catal. Commun. 2008; 9: 276
  • 9 Kiesewetter MK, Scholten MD, Kirn N, Weber RL, Hedrick JL, Waymouth RM. J. Org. Chem. 2009; 74: 9490
  • 10 Ghobril C, Sabot C, Mioskowski C, Baati R. Eur. J. Org. Chem. 2008; 4104
  • 11 Selig P, Turočkin A, Raven W. Chem. Commun. 2013; 49: 2930
  • 12 Selig P, Turočkin A, Raven W. Adv. Synth. Catal. 2013; 355: 297