4.6 Article

Synthesis of polychloromethylated and halogenated spiro[5,5]trienones via dearomative spirocyclization of biaryl ynones

Journal

ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 20, Issue 33, Pages 6659-6666

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/d2ob01053d

Keywords

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Funding

  1. Jiangsu Higher Education Institutions of China [22KJB150051, 19KJB150020]
  2. Key Project of Provincial Natural Science Research Foundation of Anhui Universities, China [KJ2020A1199]

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A selective polychloromethylation and halogenation reaction of alkynes was disclosed using a radical addition/spirocyclization cascade sequence. By utilizing polyhaloalkanes as precursors for polyhalomethyl and halogen radicals, a series of valuable spiro[5,5]trienones containing halogen-, CHCl2-, or CCl3-groups were synthesized in good yields under simple and mild conditions.
We disclosed a selective polychloromethylation and halogenation reaction of alkynes via a radical addition/spirocyclization cascade sequence, in which polyhaloalkanes were used as the precursor for polyhalomethyl and halogen radicals. Using this strategy, a series of valuable halogen-, CHCl2- or CCl3-containing spiro[5,5]trienones were synthesized in good yields with good functional group tolerance in one pot under simple and mild conditions. It is noted that an unprecedented halogenation instead of dibromomethylation was achieved when CH2Br2 was used in this work.

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