Speaker: Professor Daniel B. WERZ

Institution: Institute of Organic Chemistry, Germany

Hosted by: Professor Yangjian QUAN

Abstract

Donor-acceptor cyclopropanes (DACs) are highly strained entities which are unique building blocks for hetero- and carbocyclic systems.1,2 For the last decade, we have been developing novel methodologies starting from these type of three-membered rings leading to oligopyrroles, chalcogen-containing heterocycles, and 1,3-bisfunctionalized products,3 just to name a few. To get deeper insights into their intrinsic reactivity in-depth physical organic studies were performed recently.4 Besides the common activation of DACs by Lewis acids leading to a wide variety of ring-opening and cycloaddition products even synergistic catalytic approaches can be applied to generate fleeting intermediates which react with the strained systems. Scheme 1 depicts two representative examples, one using Lewis acid and Rh catalysis (affording intermediate carbonyl ylides)5 and another using Lewis acid and redox catalysis are presented.6 More recently, electrochemical methods were applied to activate donoracceptor cyclopropanes.7 

[1] H.-U. Reissig, R. Zimmer, Chem. Rev. 2003, 103, 1151.
[2] T. F. Schneider, J. Kaschel, D. B. Werz, Angew. Chem. Int. Ed. 2014, 53, 5504.
[3] a) J. Kaschel, T. F. Schneider, D. Kratzert, D. Stalke, D. B. Werz, Angew. Chem. Int. Ed. 2012, 51, 11153; b) A. U.
Augustin, M. Sensse, P. G. Jones, D. B. Werz, Angew. Chem. Int. Ed. 2017, 56, 14293; c) L. K. B. Garve, P. G. Jones, D. B.
Werz, D. B. Angew. Chem. Int. Ed. 2017, 56, 9226; d) G. A. Oliver, M. N. Loch, A. U. Augustin, P. Steinbach, M. Sharique,
U. K. Tambar, P. G. Jones, C. Bannwarth, D. B. Werz, Angew. Chem. Int. Ed. 2021, 60, 25825.
[4] A. Kreft, A. Lücht, J. Grunenberg, P. G. Jones, D. B. Werz, Angew. Chem. Int. Ed. 2019, 58, 1955.
[5] M. Petzold, P. G. Jones, D. B. Werz, Angew. Chem. Int. Ed. 2019, 58, 6225.
[6] A. Lücht, L. J. Patalag, A. U. Augustin, P. G. Jones, D. B. Werz, Angew. Chem. Int. Ed. 2017, 56, 10587.
[7] S. Kolb, M. Petzold, F. Brandt, P. G. Jones, C. R. Jacob, D. B. Werz, Angew. Chem. Int. Ed. 2021, 60, 15928.