Using Frustrated Lewis Pairs for Generating Stereoenriched Fluorocarbons

Project description

The proposed project is based on a synergistic partnership between the groups of Young and Singh to generate new methods for creating stereoenriched fluorocarbons via frustrated Lewis pair (FLP) mediated monoselective CF activation. Such methods will become a valuable addition to the rapidly expanding field of stereoselective fluorine chemistry, which is becoming increasingly important in the development of new fluoro-containing pharmaceuticals, agrochemicals, materials and optics. As such, the success of this project will establish a research program between UQ and IITD that will train multiple research students whilst developing an industrially and academically important area of chemistry.
Fluorocarbons are virtually non-existent in biology. Nonetheless, fluorine has had a significant impact in modern biological systems through synthetic compounds. Importantly, fluorine and fluorine containing groups act as extremely effective bioisosteres, allowing simple access to chemical antagonists and agonists. Fluorine (or a fluorine containing group) is known to emulate hydrogen, alkyl, hydroxyl and amide groups (inter alia). In a biological context, apart from chemical isostericity, stereochemistry is intrinsically important to the design of effective antagonists/agonists. Thus, it is surprising that methods for stereoselective installation of fluorine into organic molecules are belatedly undeveloped.
Given the ease of access to and the ready availability of difluoromethyl and trifluoromethyl groups, an attractive proposition to install chiral centres into polyfluoroalkyl substrates is the stereoselective functionalization of a single fluoro group, leading to stereoenriched products. Although such selective activations were a long-standing challenge in fluorine chemistry, the Young group based at UQ has developed a frustrated Lewis pair (FLP) catalysed solution that allows ready access to a wide range of singly C–F functionalized products from difluoromethyl and trifluoromethyl containg substrates.
The ability to control such reactions in a stereoselective manner would be a major advance in stereoselective fluorine chemistry and provide a new means to access stereoenriched fluorocarbons. The group of Professor Ravi Singh at IITD specializes in the development of enantioselective methodologies using covalent and non-covalent catalysis enantiomerically enriched small molecules such as alkaloid derivatives, amino acid derivatives. Their work involves the exploration of new activation modes for conquering challenging stereoselective carbon-carbon and carbon-heteroatom bond forming transformations with the help of hydrogen-bonding and bifunctional organocatalysis.

Outcomes

The design and synthesis of a new generation of chiral frustrated Lewis pair catalysts based on either chiral Lewis bases or chiral Lewis acids and the cooperative interaction of chiral Brønsted acids – Efficient and highly selective synthesis of difficult to access useful fluorinated chemical motifs from polyfluorinated started materials – Training of students in advanced organometallic and organic synthetic techniques – Student academic development to allow understanding of the relevant theories behind the discovered chemistry

Essential capabilities

Experience in organic or organometallic synthetic chemistry, solid understanding of basic chemistry concepts

Desireable capabilities

Good communication, highly motivated, previous experience in a research laboratory

Expected qualifications (Course/Degrees etc.)

a n MSc degree in chemistry or related field

Additional information for applicants

note: i-students must have own scholarship to apply (CSIR, UCG-NET, etc)