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Iron‐Catalyzed Regioselective Alkenylboration of Olefins
Author(s) -
Yu Xiaolong,
Zheng Hongling,
Zhao Haonan,
Lee Boon Chong,
Koh Ming Joo
Publication year - 2021
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202012607
Subject(s) - regioselectivity , chemistry , olefin fiber , alkene , bromide , structural isomer , catalysis , cleavage (geology) , yield (engineering) , halide , medicinal chemistry , fluoride , chloride , organic chemistry , inorganic chemistry , materials science , geotechnical engineering , fracture (geology) , engineering , metallurgy
The first examples of an iron‐catalyzed three‐component synthesis of homoallylic boronates from regioselective union of bis(pinacolato)diboron, an alkenyl halide (bromide, chloride or fluoride), and an olefin are disclosed. Products that bear tertiary or quaternary carbon centers could be generated in up to 87 % yield as single regioisomers with complete retention of the olefin stereochemistry. With cyclopropylidene‐containing substrates, ring cleavage leading to trisubstituted E ‐alkenylboronates were selectively obtained. Mechanistic studies revealed reaction attributes that are distinct from previously reported alkene carboboration pathways.