Early-Stage Organocatalysis

Introduction

Organocatalysis has drastically advanced stereoselective chemical synthesis. From an underdeveloped niche area, it has become the most frequently applied approach to asymmetric synthesis. Organocatalysis is also developing into a technology that can be used to make pharmaceuticals, scents, and other fine chemicals.

Current Challenges

However, the early stages of industrial chemistry, specifically the upgrading of hydrocarbon-based alkenes, arenes, and alkanes, are still largely dominated by heterogeneous and transition metal catalysts.

Research Question

Here we will address the question of whether a selective Early-Stage Organocatalysis (ESO) can be developed that directly delivers high-value substances from abundantly available hydrocarbon feedstock chemicals, while significantly saving energy and other resources.

Recent Developments

During the last few years, we have developed confined organic acids as a new catalyst class that features enzyme and zeolite-inspired active sites with well-defined pockets for selective substrate recognition and catalysis.

These catalysts offer a widely tunable reactivity range, reaching extreme levels with turnover numbers exceeding 10^6 in challenging asymmetric carbon-carbon bond forming reactions, and approaching magic acid reactivity toward the activation of olefins.

Future Aims

We now aim to take confined acid catalysis to another level by designing new, even more reactive acids that enable the utilization and valorization of steam-cracker-based hydrocarbons in selective organocatalysis. Specifically, we propose three aims:

1. Developing asymmetric olefin hydrofunctionalizations including hydrations and hydroarylations.
2. An early stage functionalization of simple arenes such as benzene and toluene via highly stereoselective and regioselective electrophilic aromatic substitution reactions.
3. As the ultimate test of extreme reactivity, we propose organocatalytic, asymmetric reactions of alkanes.

Conclusion

The all-underlying goal will be the design and development of organocatalysts of the next generation.