One-Pot Synthesis of
2,4-Diacyl Thiophenes from α‑Oxo
Ketene Dithioacetals and Propargylic Alcohols
Posted on 2020-07-24 - 21:14
Although thiophenes having various
functionalities are the basic
structural units in numerous bioactive compounds and optoelectronic
materials, synthetic routes to acylated thiophenes from aliphatic
sulfur-containing starting materials are still rare. In particular,
there have been no reports concerning the straightforward synthesis
of 2,4-diacylthiophenes from alkynes. Herein, we describe a highly
efficient and metal-free three-step one-pot synthetic approach to
tetrasubstituted 2,4-diacylthiophenes from propargylic alcohols and
α-oxo ketene dithioacetals. This research features a relay catalysis
system that integrates Brønsted acid-catalyzed propargylation,
molecular iodine-mediated electrophilic cyclization, and visible light-induced
deiodinative oxygenation. The 2,4-diacylthiophenes serving as the
key starting materials are readily synthesized, enabling facile construction
of analogues of related biologically active compounds and the modular
assembly of tetrasubstituted thienothiophenes.
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Xue, Jian; Bai, Li-Gang; Zhang, Liang; Zhou, Yue; Lin, Xiao-Long; Mou, Neng-Jie; et al. (2020). One-Pot Synthesis of
2,4-Diacyl Thiophenes from α‑Oxo
Ketene Dithioacetals and Propargylic Alcohols. ACS Publications. Collection. https://doi.org/10.1021/acs.joc.0c01093