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Divergent gold-catalysed reactions of cyclopropenylmethyl sulfonamides with tethered heteroaromatics

Journal Article


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Abstract


  • Cyclopropenylmethyl sulfonamides with tethered heteroaromatics have been demonstrated to undergo divergent gold-catalysed cyclisation reactions. A formal dearomative (4+3) cycloaddition takes place with furan-tethered substrates, yielding densely functionalised 5,7-fused heterocycles related to the bioactive curcusone natural products. Indole-tethered substrates display divergent reactivity giving biologically important tetrahydro-β-carbolines via a Friedel-Crafts mechanism.

UOW Authors


  •   Drew, Melanie A. (external author)
  •   Arndt, Sebastian (external author)
  •   Richardson, Christopher
  •   Rudolph, Matthias (external author)
  •   Hashmi, A. Stephen K. (external author)
  •   Hyland, Christopher

Publication Date


  • 2019

Citation


  • Drew, M. A., Arndt, S., Richardson, C., Rudolph, M., Hashmi, A. K. & Hyland, C. J.T. (2019). Divergent gold-catalysed reactions of cyclopropenylmethyl sulfonamides with tethered heteroaromatics. Chemical Communications, 55 (93), 13971-13974.

Scopus Eid


  • 2-s2.0-85075227785

Ro Full-text Url


  • https://ro.uow.edu.au/cgi/viewcontent.cgi?article=2051&context=smhpapers1

Ro Metadata Url


  • http://ro.uow.edu.au/smhpapers1/1037

Number Of Pages


  • 3

Start Page


  • 13971

End Page


  • 13974

Volume


  • 55

Issue


  • 93

Place Of Publication


  • United Kingdom

Abstract


  • Cyclopropenylmethyl sulfonamides with tethered heteroaromatics have been demonstrated to undergo divergent gold-catalysed cyclisation reactions. A formal dearomative (4+3) cycloaddition takes place with furan-tethered substrates, yielding densely functionalised 5,7-fused heterocycles related to the bioactive curcusone natural products. Indole-tethered substrates display divergent reactivity giving biologically important tetrahydro-β-carbolines via a Friedel-Crafts mechanism.

UOW Authors


  •   Drew, Melanie A. (external author)
  •   Arndt, Sebastian (external author)
  •   Richardson, Christopher
  •   Rudolph, Matthias (external author)
  •   Hashmi, A. Stephen K. (external author)
  •   Hyland, Christopher

Publication Date


  • 2019

Citation


  • Drew, M. A., Arndt, S., Richardson, C., Rudolph, M., Hashmi, A. K. & Hyland, C. J.T. (2019). Divergent gold-catalysed reactions of cyclopropenylmethyl sulfonamides with tethered heteroaromatics. Chemical Communications, 55 (93), 13971-13974.

Scopus Eid


  • 2-s2.0-85075227785

Ro Full-text Url


  • https://ro.uow.edu.au/cgi/viewcontent.cgi?article=2051&context=smhpapers1

Ro Metadata Url


  • http://ro.uow.edu.au/smhpapers1/1037

Number Of Pages


  • 3

Start Page


  • 13971

End Page


  • 13974

Volume


  • 55

Issue


  • 93

Place Of Publication


  • United Kingdom