Installation of O‐Heterocycles to N‐Heteroarenes via an Et 3 B/O 2 ‐Mediated Radical Reaction of α‐Alkoxy and α‐Alkoxyacyl Tellurides

We report a radical‐based method that links highly oxygenated O‐heterocycles and N‐heteroarenes. Treatment of α‐alkoxy or α‐alkoxyacyl tellurides with Et 3 B under air at room temperature generated α‐alkoxy carbon radicals, which were then added to protonated N‐heteroarenes. Regeneration of aromatic...

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Bibliographic Details
Published in:Asian journal of organic chemistry 2019-07, Vol.8 (7), p.1088-1091
Main Authors: Kuwana, Daiki, Ovadia, Benjamin, Kamimura, Daigo, Nagatomo, Masanori, Inoue, Masayuki
Format: Article
Language:English
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Summary:We report a radical‐based method that links highly oxygenated O‐heterocycles and N‐heteroarenes. Treatment of α‐alkoxy or α‐alkoxyacyl tellurides with Et 3 B under air at room temperature generated α‐alkoxy carbon radicals, which were then added to protonated N‐heteroarenes. Regeneration of aromaticity proceeded in situ without an additional oxidant, leading to O‐heterocycle‐functionalized N‐heteroarenes. The present method enables the formation of hindered C(sp 3 )−C(sp 2 ) bonds between five O‐heterocycles and five N‐heteroarenes under mild conditions.
ISSN:2193-5807
2193-5815
DOI:10.1002/ajoc.201900170