Halides are highly reactive in nature and thus, can be easily functionalised to other useful products
by known methods including cross coupling, amination, arylation, borylation, alkoxylation,
alkylation reactions, etc.1 Chiral halogen containing compounds serve as essential building blocks for
the preparation of complex molecules in medicinal chemistry and chiral precursors in the formation
of C-C bonds as well as various carbon-heteroatom bonds.2 Introduction of one or more halogen
atoms into organic molecules is one of the most important transformations in organic synthesis. Most
reports employ Lewis acid and Lewis base reagents as catalysts for the asymmetric halogenation.
This research proposal seminar focuses on the enantioselective electrophilic halocyclization,3 α-
halogenations of carbonyl compound,4 diastereoselective halogenations of alkenes,5 lactonization and
aromatic halogenation using Lewis base and Lewis acid catalysts (Scheme 1). Sulfur containing
catalysts show high catalytic activity in halogenation reactions. However, asymmetric halogenation
reactions utilizing chiral sulfur containing catalyst has been scarcely reported. This research proposal
seminar will explore new sulfur containing catalysts for asymmetric halogenation reactions.
Scheme 1. Asymmetric halogenation reactions.
References
1. Shi, H.; Wang, P.; Suzuki, S.; Farmer, M. E.; Yu, J. Q. J. Am. Chem. Soc., 2016, 138, 14876−14879
2. Cantillo, D.; Kappe, C. O. React. Chem. Eng., 2017, 2, 7−19.
3. Sakakura, A.; Ukai, A.; Ishihara, K. Nature., 2007, 445, 900-903.
4. Ueda, M.; Kano, T.; Maruoka, K. Org. Biomol. Chem., 2009, 7, 2005–2012
5. Denmark, S. E.; Kuester, W. E.; Burk, M. T. Angew. Chem. Int. Ed., 2012, 51, 2–18.