Photo-induced Carboiodination: A Simple Way to Synthesize Functionalized Dihydrobenzofurans and Indolines
Xiaobo Yang1,2, Wenbo Liu1, Lu Li1
1Department of Chemistry and FQRNT Centre for Green Chemistry and Catalysis, McGill University, 801 Sherbrooke St. W., Montreal, Quebec, H3A 0B8, Canada.
Abstract:
Herein, we report a simple, redox-neutral and pH-neutral photo-induced carboiodination reaction under very mild conditions. This protocol employs readily available and cheap aryl bromides and sodium iodide as the starting materials to synthesize valuable functionalized dihydrobenzofurans and indolines in good to excellent yields with broad functional-group compatibility. As examples to demonstrate the utility of this protocol, gram-scale reactions and further transformations of the products were accomplished towards the synthesis of bioactive drug candidates. Most significantly, to the best of our knowledge, this reaction represents the first example of a cascade atom-radical-transfer addition involving the cleavage of aromatic C-Br bond.
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