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© Matthias Scherr

Inves­ti­ga­tion of the influ­ence of steri­cally challeng­ing NHC gold(I) complexes in di-cyclizations

Matthias Scherr — Hector Fellow A. Stephen K. Hashmi

The research project inves­ti­gates the influ­ence of steri­cally demand­ing NHC-gold(I) complexes on the cycliza­tion of diyne deriv­a­tives. The focus is on the synthe­sis of various steri­cally demand­ing NHC-gold(I) complexes and their appli­ca­tion in diyne cycliza­tions, partic­u­larly examin­ing the reactiv­ity and selec­tiv­ity in gold-catalyzed reactions. Further inves­ti­ga­tions include theoret­i­cal calcu­la­tions and practi­cal appli­ca­tions of the synthe­sized cycliza­tion products for pharma­ceu­ti­cals or organic materials.

The research project inves­ti­gates the influ­ence of steri­cally demand­ing N‑heterocyclic carbene-gold(I) complexes on the cycliza­tion of diynes. A partic­u­lar focus is placed on the synthe­sis of various steri­cally demand­ing NHC-gold(I) complexes and their appli­ca­tion as catalysts in diyne cycliza­tions. The study explores the reactiv­ity and selec­tiv­ity in gold-catalyzed reactions. Initial studies indicate that steri­cally demand­ing NHC-gold(I) complexes overcom­pen­sate the electronic influ­ence of the metal center without reduc­ing its reactivity.

Further inves­ti­ga­tions include quantum chemi­cal calcu­la­tions and practi­cal appli­ca­tions of the synthe­sized cycliza­tion products in pharma­ceu­ti­cals and organic materi­als. By varying the backbone of the diynes, intro­duc­ing differ­ent substituents, and using various solvents, the project aims to test the limits of the catalytic system. Addition­ally, bidirec­tional approaches and the use of triyne systems are consid­ered. Moreover, the applic­a­bil­ity of the catalytic system to En-Yne and En-En cycliza­tions will be examined.

The goal is to enable targeted control of selec­tiv­ity in gold-catalyzed diyne cycliza­tion through catalyst varia­tion. Further­more, the project will uncover new catalytic pathways and is extend­able to other NHC-metal complexes. The mecha­nis­tic insights gained from this research will not only deepen the under­stand­ing of gold catal­y­sis but also promote the devel­op­ment of new appli­ca­tions in organic materi­als and pharmaceuticals.

Untersuchung des Einflusses von sterisch hoch anspruchsvollen NHC-Gold(I)-Komplexen in Diinzyklisierungen

Mecha­nis­tic reaction pathways of di-cycli­sa­tions with NHC-Gold(I) complexes using the steri­cally less demand­ing IPrAuCl ([Au]) and a steri­cally highly demand­ing NHC-Gold(I) complex ([Au]).

Laure Ciernik

Matthias Scherr

Heidel­berg University

Super­vised by

Prof. Dr.

A. Stephen K. Hashmi

Chemistry

Hector Fellow since 2010Disziplinen A. Stephen K. Hashmi