α-Monoarylation and Tandem Arylation-Insertion of Malonates with Arynes

来源 :第五届岭南有机化学论坛暨华南理工大学-兰州大学有机化学双边论坛 | 被引量 : 0次 | 上传用户:man416784150
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Aryne chemistry has been of particular interest due to its high reactivity and broad applications in organic synthesis.The nucleophilic additions of aromatic acids,phenols,sulfonamides,amines,β-enamino esters/ketones,amides,hydrazones,6 and cyclic ethers to highly electrophilic arynes,which were generated by fluoride-induced elimination of Kobayashis silylaryl triflates,have been achieved to afford various arylation products.However,the α-arylation of active methylene compounds,which provides a facile methodology for the synthesis of bioactive natural/synthetic products,has not been well documented when arynes were employed as the aryl sources.Herein,we report an efficient α-monoarylation and tandem arylation-insertion of malonates with arynes using Kobayashis precursors to afford α-arylmalonates in good yields with high chemoselectivities and diarylmethane derivatives in good yields under mild conditions.The arylation of other 1,3-dicarbonyl compounds has also been investigated.(Scheme 1).
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