Cooperative Photoinduced/Brønsted Acid Catalyzed Cycloaddition of Transient Thioaldehydes and ortho-Quinone Methides toward a Synthesis of Benzo[e][1,3]oxathiines.
Cooperative Photoinduced/Brønsted Acid Catalyzed Cycloaddition of Transient Thioaldehydes and ortho-Quinone Methides toward a Synthesis of Benzo[e][1,3]oxathiines.
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光诱导/布朗斯台德酸催化瞬时硫醛和邻醌甲基化物的环加成反应合成苯并[e][1,3]氧噻啶
DOI：
10.1021/acs.orglett.1c00588
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发表时间：
2021
期刊：
影响因子：
5.2
通讯作者：
C. Schneider
中科院分区：
文献类型：
--
作者：
F. Sachse;C. Schneider
本文提出了一种协同的一锅法，分别在紫外光照射和布朗斯特酸催化下，原位生成硫代醛和邻醌甲基化物，然后进行环加成反应，得到苯并[e][1，3]恶硫杂环戊二烯，收率和非对映选择性都很好。富电子和贫电子的硫代醛在室温下都能与大量的苯醌甲基化物在短时间内反应生成多种硫杂环化合物。
A cooperative, one-pot approach for the in situ generation and ensuing cycloaddition of thioaldehydes andortho-quinone methides transiently formed under irradiation with UV-A light and Brønsted acid catalysis, respectively, has been developed giving direct access to benzo[e][1,3]oxathiines in good to excellent yields and diastereoselectivity. Both electron-rich and electron-poor thioaldehydes easily react with a broad range ofortho-quinone methides at ambient temperature in a short reaction time to furnish a wide variety ofS,O-heterocycles.