Sequential olefination-dimerisation of benzylic dithioacetals by the nickel-catalysed reaction with methyl Grignard or zinc reagent

Products of main group elements from cross-coupling reactions have been shown to serve as Lewis acids, mediating further reactions of organic coupling products. Thus, the nickel-catalysed olefination of benzylic dithioacetal with MeMgI in benzene in a sealed Schlenk tube at 130 °C generates magnesiu...

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Bibliographic Details
Published in:RSC advances 2022-03, Vol.12 (16), p.9653-9659
Main Authors: Yu, Lei, Lai, Guo-Qiao, Zhang, Pinglu, Li, Ze, Luh, Tien-Yau
Format: Article
Language:English
Subjects:
Benzene
Chemical reactions
Chemistry
Cross coupling
Dimers
Lewis acid
Magnesium
Nickel
Reagents
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Summary:Products of main group elements from cross-coupling reactions have been shown to serve as Lewis acids, mediating further reactions of organic coupling products. Thus, the nickel-catalysed olefination of benzylic dithioacetal with MeMgI in benzene in a sealed Schlenk tube at 130 °C generates magnesium mercaptide which regioselectively converts 2-arylpropene into a dimer in good yield. Aryl iodide reacts with 2-propenylmagnesium bromide in the presence of 1,2-ethanedithiol and NiCl 2 (PPh 3 ) 2 to yield the same dimer. Replacement of the Grignard reagent by an organozinc reagent gives the dimers in a better yield. The nickel-catalyzed olefination of benzylic dithioacetal with MeMgI or the corresponding zinc reagent generates Mg( ii ) or Zn( ii ) mercaptide which converts 2-arylpropene into dimer regioselectively.
ISSN:2046-2069
2046-2069
DOI:10.1039/d2ra00841f