Divergence in the reactivity between amine- and phosphine-catalyzed cycloaddition reactions of allenoates with enynals: one-pot gold-catalyzed synthesis of trisubstituted benzofurans from the [3 + 2] cycloadduct via 1,2-alkyl migration and dehydrogenation

The Journal of Organic Chemistry
A Leela Siva Kumari, K C Kumara Swamy

Abstract

Regioselective synthesis of functionalized dihydropyran derivatives by DABCO-catalyzed [2 + 4] cycloaddition of allenoates with enynals or enynones has been developed. Phosphine-catalyzed [3 + 2] cycloaddition of allenoates with enynals provides 1,1-alkyne (aldehyde)-substituted cyclopentenes wherein enynals act as electrophiles. These alkyne-tethered cyclopentenes upon [Au]/[Ag] catalysis lead to substituted benzofurans via 1,2-alkyl migration and dehydrogenation (aromatization). One-pot reaction of allenoates with enynals using sequential phosphine and gold catalysis is also reported. The cyclopentene obtained from the PPh3-catalyzed reaction of allenoate H2C═C═CH(COO-t-Bu) with enynal undergoes decarboxylation under the [Au]/[Ag] catalysis and forms a carboxylate-free benzofuran. The structures of key products are confirmed by single-crystal X-ray analysis.

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Citations

Jun 16, 2016·Organic & Biomolecular Chemistry·A Leela Siva KumariK C Kumara Swamy
Oct 11, 2016·Organic & Biomolecular Chemistry·Aurélien BlancPatrick Pale
Oct 30, 2020·Organic & Biomolecular Chemistry·Zhen-Zhen XieHua Yang
May 4, 2018·Organic Letters·Mi-Na ZhaoZheng-Hui Guan
Sep 28, 2018·Chemical Reviews·Hongchao GuoOhyun Kwon
Nov 3, 2021·Organic & Biomolecular Chemistry·Maria I L SoaresTeresa M V D Pinho E Melo

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