Versatile building blocks to synthesise organic molecules faster and more efficiently”

Organic molecules comprise of a carbon-based framework decorated with ‘functional groups’ – parts that can be used in their construction and for tuning important properties, such as shape, solubility, biological activity, luminescence and more. Chemists are able to make almost any organic molecule, but few complex molecules can be made efficiently.

One idealised approach to buildling complex molecules efficiently is to design “building blocks” that carry multiple versatile functional groups and learn to use each without affecting the others. The uneffected groups can be valuable for use further along in the synthesis or for tuning properties later.

In this study we showed that two extremely versatile functional groups – a boron-based group and a very reactive CºC bond – tolerate each other in this sense; either one can be activated and transformed to very many different new groups, or used to build up the molecule, without any damage to the other. Incorporating both groups on one molecule is therefore a promising approach to a good “building block”.  

Our approach has two further, major benefits. Firstly, the boron-based group can easily be introduced to commercially available starting materials, simply by substituting a C-H bond using a special catalyst. This makes preparation of our buildling blocks incredibly convenient. Secondly, it appears that the two functional groups not only tolerate each other, but actually ‘enhance’ each others’ reactivity in valuable ways.

Orginalartikel: Boryl (Hetero)aryne Precursors as Versatile Arylation Reagents:

Synthesis through C¢H Activation and Orthogonal Reactivity, https://onlinelibrary.wiley.com/doi/full/10.1002/anie.201503152, Angew Chem Int Ed Engl. 2015 Sep 28; 54(40): 11765–11769.

Emilien Demory, Karthik Devaraj, Andreas Orthaber, Paul J. Gates, and Lukasz T. Pilarski*

Lukasz T.Pilarski undervisar på följande kurser på institutionen för kemi:

Syllabus for Coordination and Organometallic Chemistry  (5 credits)
https://www.uu.se/en/admissions/master/selma/kursplan/?kpid=38146&typ=1

Modern Methods in Organic Synthesis 2019/2020 (10credits)
https://www.uu.se/en/admissions/freestanding-courses/course/?kKod=1KB443&typ=1

Organic Chemistry I 2019/2020 (10 credits)
länk saknas, kursstart mars 2020

Organic Synthesis 2019/2020 (15 credits),
https://uu.se/en/admissions/freestanding-courses/course/?kKod=1KB451&typ=1

Länk till Lukazs forskargrupp: https://pilarskigroup.org/