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Michael Schnurch

Speaker for catalysis 2017 - Michael Schnurch

Title: Decoration of acyclic amines via metal catalyzed C-H activation reactions

Michael Schnurch

TU Wien, Austria

Biography

Assoc. Prof. Michael Schnürch studied Chemistry at TU Wien and did his Masters as well as PhD thesis under the supervision of Prof. Peter Stanetty. During his PhD thesis, he conducted a four months internship with Prof. Victor Snieckus at the Queen´s University in Kingston, Ontario, Canada. He then went on to a postdoctoral stay as Erwin Schrödinger Fellow with Prof. Dalibor Sames at the Columbia University in New York. After his return to Vienna, he started his independent career and finished his habilitation in 2013. In 2016 he was promoted to Associate Professor in the field of organometallic chemistry.

Abstract

Metal catalyzed C-H activation chemistry can be considered as the logic advancement of cross-coupling chemistry (e.g. the famous Suzuki-Miyaura reaction). Instead of using two pre-functionalized reaction partners, the C-H bond itself is used as functional group. This bears the potential for a significant improvement regarding step economic synthesis of complex compounds. C-C bond forming processes are the most important reactions for building up the skeletons of organic molecules. Alkylation and arylation reactions are frequently applied transformations in this field. Many different aryl sources have been used in metal catalyzed C-H activation reactions. Also we contributed to this field by investigating the -arylation of aliphatic acyclic amines. Three different protocols were developed, which all proceed via distinctively different mechanisms and hence, require a specific set of reaction conditions. This allows using the transformation which reaction conditions are best compatible with a given substrate.
In the field of direct alkylation, we will report on a new type of alkyl source as alternative to the frequently applied olefins. Olefins have the drawback that the short chained representatives are gaseous at room temperature, and hence high pressure equipment has to be used in many cases. Our development makes this special equipment obsolete and alkylation reactions, including ethylations, can be carried out in standard glassware. The applied reagents are solid materials and stable at ambient conditions for a prolonged time. This leads to operationally simpler and safer alkylation reactions, which in turn will surely increase the number of applications for these processes.
Furthermore, mechanistic and kinetic studies will be presented, leading to the proposal of a reaction mechanism for all of the reported transformations.

Audience Take away:

•    The direct functionalization of aliphatic amines in alpha position will be presented.
•    Methods for arylation and alkylation will be discussed. For arylation, three different aryl sources were investigated, which result also in different mechanisms operable. This allows choosing for the same reaction the type of transformation which suits best to the respective problem.
•    For alkylation, a new type of alkyl source was identified, which makes the use of high pressure equipment obsolete, as opposed to the most frequently applied olefins as aryl source. This allows significantly safer and operationally simpler alkylation processes.
•    Kinetic and mechanistic studies will give insight into this reaction archetype.