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Unusual (Z)-selective palladium(II)-catalysed addition of aryl boronic acids to vinylaziridines

Journal Article


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Abstract


  • The palladium(II)-catalysed addition of arylboronic acids to vinylaziridines has been developed. This reaction proceeds via an insertion/ring-opening process to provide (Z)-allylsulfonamides preferentially. This stereoselectivity is complimentary to existing methods that typically proceed via a SN2′ mechanism to yield (E)-allylsulfonamides. Electron-deficient arylboronic acids were the optimum substrates for this reaction, while electron-donating groups on the aromatic ring of the boronic acids resulted in moderate yields.

UOW Authors


  •   Yin, Jiexiang (external author)
  •   Mekelburg, Theresa (external author)
  •   Hyland, Christopher

Publication Date


  • 2014

Citation


  • Yin, J., Mekelburg, T. & Hyland, C. (2014). Unusual (Z)-selective palladium(II)-catalysed addition of aryl boronic acids to vinylaziridines. Organic and Biomolecular Chemistry, 12 (45), 9113-9115.

Scopus Eid


  • 2-s2.0-84908688812

Ro Full-text Url


  • http://ro.uow.edu.au/cgi/viewcontent.cgi?article=3335&context=smhpapers

Ro Metadata Url


  • http://ro.uow.edu.au/smhpapers/2317

Number Of Pages


  • 2

Start Page


  • 9113

End Page


  • 9115

Volume


  • 12

Issue


  • 45

Abstract


  • The palladium(II)-catalysed addition of arylboronic acids to vinylaziridines has been developed. This reaction proceeds via an insertion/ring-opening process to provide (Z)-allylsulfonamides preferentially. This stereoselectivity is complimentary to existing methods that typically proceed via a SN2′ mechanism to yield (E)-allylsulfonamides. Electron-deficient arylboronic acids were the optimum substrates for this reaction, while electron-donating groups on the aromatic ring of the boronic acids resulted in moderate yields.

UOW Authors


  •   Yin, Jiexiang (external author)
  •   Mekelburg, Theresa (external author)
  •   Hyland, Christopher

Publication Date


  • 2014

Citation


  • Yin, J., Mekelburg, T. & Hyland, C. (2014). Unusual (Z)-selective palladium(II)-catalysed addition of aryl boronic acids to vinylaziridines. Organic and Biomolecular Chemistry, 12 (45), 9113-9115.

Scopus Eid


  • 2-s2.0-84908688812

Ro Full-text Url


  • http://ro.uow.edu.au/cgi/viewcontent.cgi?article=3335&context=smhpapers

Ro Metadata Url


  • http://ro.uow.edu.au/smhpapers/2317

Number Of Pages


  • 2

Start Page


  • 9113

End Page


  • 9115

Volume


  • 12

Issue


  • 45