A facile metal-free one-flask synthesis of multi-substituted furans via a BF3·Et2O mediated formal [4 + 1] reaction of 3-chloro-3-phenyldiazirines and α,β-alkenyl ketones |
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| Authors: | Zixin Zhang Aimin Huang Lin Ma Jian-hua Xu Min Zhang |
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| Affiliation: | School of Chemistry and Chemical Engineering, Guangxi University, Nanning Guangxi 530004 China.; School of Chemistry and Chemical Engineering, Nanjing University, Nanjing Jiangsu 210093 China |
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| Abstract: | A facile, efficient and metal free one-flask approach to diversely substituted furans from easily accessible 3-chloro-3-phenyldiazirines and α,β-alkenyl ketones is reported. This protocol integrates three steps of cyclopropanation, Cloke–Wilson rearrangement and elimination of HCl in one-flask to give products in moderate to good yields. It provides a metal and oxidant free approach to multi-substituted furans with the advantages of easy operation, mild reaction conditions and a broad scope of substrates.A metal and oxidant free approach to multi-substituted furans from easily accessible 3-chloro-3-phenyldiazirines and α,β-alkenyl ketones in one flask. |
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