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Efficient Assembly of Chromone Skeleton from 2,3-Allenoic Acids and Benzynes

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journal contribution
posted on 07.10.2011, 00:00 authored by Guobi Chai, Youai Qiu, Chunling Fu, Shengming Ma
Chromone derivatives were synthesized from 2,3-allenoic acids and benzynes in moderate to excellent yields under mild conditions. Instead of the cyclic conjugate addition of the intermediate A formed by the nucleophilic addition of allenoic acid with benzyne, this intermediate undergoes 1,2-addition with the carbonyl group, which was followed by the ring opening, conjugate addition, and protonolysis to afford chromone derivatives. This protocol allows the diversity due to the substituent-loading capability of 2,3-allenoic acids as well as benzynes.