TripIod · Development of Triptycene-Based New Hypervalent Iodine Reagents for Selective Organic Synthesis

Development of Triptycene-Based New Hypervalent Iodine Reagents for Selective Organic Synthesis

Initially, we prepared triptycene core structure bearing iodine at position–1 or –2 in one of the aromatic rings. Subsequently, chiral iodotriptycene compounds such as 1–chloro–7–iodotriptycene and 5-iodo-1,4-dimethoxytriptycene have been prepared and their enantiomers were separated and isolated using preparative chiral HPLC method and chiral resolution method. The absolute configuration of each of the isolated enantiomers of 5-iodo-1,4-dimethoxytriptycene was determined by single crystal X-ray structures having a high HPLC purity. Prepared iodotriptycenes were investigated in a catalytic manner for the α-oxytosylation of propiophenone, yields were good but enantioselectivities was generally not high. 1. To developed a strategy to prepare novel iodotriptycene reagents and use of 1,4-dimethoxyanthracene to avoid diastereomers formation. 2. To investigate activity of iodotriptycenes as a catalysts in organic transformations of α–oxytosylation of propiophenone. 3. To use enantiomers of 1-chloro-7-iodotriptycene and 5–iodo–1,4–dimethoxytriptycene in stereoselective reactions of α-oxytosylation of propiophenone. 4. To use iodotriptyce in making 2-(diacetoxyiodo)-triptycene and to utilize 5–iodo–1,4–dihydroxytriptycene in polymer synthesis. 5. To use iodotriptycene in flow electrochemistry by oxidizing it with electric current. 6. To train Dr. Khan with skills required for enantioselective reactions that previously he has not been experienced including hands on experience for electrochemistry in flow and non-scientific training. We have prepared “iodotriptycenes” including their chiral analogues whose core structure possesses features to show non-covalent interactions. They show good catalytic activity in organic transformation of α-oxytosylation of propiophenone but with low enantioselectivity. In the area of hypervalent iodine chemistry these are promising new catalyst. Developed new methods would be useful informations in making chiral triptycene compounds in material chemistry, polymer chemistry or in supramolecular chemistry and non-metal triptycene based catalyst. We have established a reliable approach for the synthesis of iodotriptycenes and their chiral analogues and are proven efficient new metal free catalyst in organic transformations (eg. α-oxytosylation). Although enantioinduction of these new chiral iodotriptycene catalysts are generally low, we hope this work serves as a basis for further research in this area, which is key for progression.

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