Optimization and Investigation of a Photoredox-Driven Selective Radical Cyclization Open Access
Tuncaral, Defne (Spring 2024)
Abstract
Advancements in pharmaceutical chemistry require innovation on organic synthesis methodology to produce complex molecules in a mild and efficient manner. Within this context, radical cascade reactions have played a pivotal role in complex molecule synthesis given their high selectivities and functional group tolerance. We aimed to advance this field by developing a photoredox-driven aryl radical cyclization/hydroxylation cascade using abundant aryl halide radical precursors and O2 for carbon-oxygen bond formation. The products of these reactions would be medicinally relevant, highly functionalized indane cores where the pendant alcohol could be used for further functionalization.
Our reaction design utilizes a halogen atom abstraction (XAT) radical generation approach that enables radical reactivity in the presence of O2. With this reaction design we were able to conduct a number of high yielding 5-exo, as well as 6-exo, radical cyclization/hydroxylation cascades. Included in these results are medicinally relevant motifs such as indanes, benzofurans, indolines, and chromanes with yields in the range of 45-91%. Future work entails further exploring aryl radical reactivity in the presence of O2 for additional cascade/hydroxylation reactions.
Table of Contents
Introduction 1
Results and Discussion 7
Conclusion and Future Directions 15
References 17
Methods 21
Supplemental Information 31
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Optimization and Investigation of a Photoredox-Driven Selective Radical Cyclization () | 2024-04-10 11:52:04 -0400 |
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