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Facile Synthesis of α‐Haloketones by Aerobic Oxidation of Olefins Using KX as Nonhazardous Halogen Source
Author(s) -
Luo Zhibin,
Meng Yunge,
Gong Xinchi,
Wu Jie,
Zhang Yulan,
Ye LongWu,
Zhu Chunyin
Publication year - 2020
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201900372
Subject(s) - chemistry , electrophile , halogen , yield (engineering) , catalysis , halide , reaction conditions , combinatorial chemistry , photochemistry , organic chemistry , alkyl , materials science , metallurgy
Summary of main observation and conclusion An operationally simple and safe synthesis of α‐haloketones using KBr and KCl as nonhazardous halogen sources is reported. It involves an iron‐catalysed reaction of alkenes with KBr/KCl using O 2 as terminal oxidant under the irradiation of visible‐light. This strategy avoids the risks associated with handling halo‐contained electrophiles (Cl 2 , Br 2 , NCS, NBS). The process is tolerant to several functional groups, and extended to a range of substituted styrenes in up to 89% yield. A radical reaction pathway is proposed based on control experiments and spectroscopy studies.