1,3- and 1,4-Benzdiyne equivalents for regioselective synthesis of polycyclic heterocycles

Chemical Science
Takashi IkawaShuji Akai

Abstract

We have devised a novel 1,3-benzdiyne equivalent, capable of quadruple functionalization by sequential benzyne generation and reaction with arynophiles. The key features of this method include the chemoselective generation of two triple bonds in a single benzene ring under fluoride-mediated mild conditions, and the regiocontrol of each benzyne reaction by the substituent next to the triple bond. This method produced various benzo-fused heteroaromatic compounds via reactions with arynophiles, such as furans, azides, and diazo compounds. A validation of the method is given in the convergent synthesis of the antipsychotic drug risperidone. A similar strategy has also been applied to a 1,4-benzdiyne equivalent to construct linearly benzo-fused heteroaromatics.

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Citations

May 9, 2019·Chemical Society Reviews·Marcus Korb, Heinrich Lang
Dec 7, 2018·Chemical & Pharmaceutical Bulletin·Takashi IkawaShuji Akai
Jul 7, 2018·Beilstein Journal of Organic Chemistry·Veronika HladíkováJiří Hanusek
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Dec 31, 2016·Journal of the American Chemical Society·Jiarong ShiYang Li
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Mar 2, 2017·The Journal of Organic Chemistry·Takashi IkawaShuji Akai
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