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Installation of O‐Heterocycles to N‐Heteroarenes via an Et 3 B/O 2 ‐Mediated Radical Reaction of α‐Alkoxy and α‐Alkoxyacyl Tellurides
Author(s) -
Kuwana Daiki,
Ovadia Benjamin,
Kamimura Daigo,
Nagatomo Masanori,
Inoue Masayuki
Publication year - 2019
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201900170
Subject(s) - chemistry , alkoxy group , radical , protonation , medicinal chemistry , carbon fibers , organic chemistry , ion , alkyl , materials science , composite number , composite material
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.