Soumitra Majee, Sangram Samanta, Dinabandhu Samanta, Modhu Sudan Maji
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引用次数: 0
Abstract
The directing group free alkenylation of indoles is underdeveloped and a highly desirable transformation in the field of π-excessive heterocycle chemistry. In this study to access C2-alkenylindoles, 3-chloroindoles were utilized as C2-indolyl electrophiles toward allyl boronic acid nucleophiles. This approach provides access to NH-free C2-alkenylindoles bearing no substitution at their C3-position. The reversed-allylated products underwent in situ isomerization under the influence of Lewis acidic allyl boronic acid, eventually delivering the desired 2-alkenyl indoles. A range of electronically different indoles took part in this reaction, providing products in good yields, and diastereoselectivities vary depending on the steric nature of allyl moieties. Synthesis of carbazole-based alkaloids hyellazole and 6-chlorohyellazole demonstrated the synthetic utility of this one-pot cascade protocol.
期刊介绍：
Helvetica Chimica Acta, founded by the Swiss Chemical Society in 1917, is a monthly multidisciplinary journal dedicated to the dissemination of knowledge in all disciplines of chemistry (organic, inorganic, physical, technical, theoretical and analytical chemistry) as well as research at the interface with other sciences, where molecular aspects are key to the findings. Helvetica Chimica Acta is committed to the publication of original, high quality papers at the frontier of scientific research. All contributions will be peer reviewed with the highest possible standards and published within 3 months of receipt, with no restriction on the length of the papers and in full color.
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