N-Sulfonylcarboxamide as an Oxidizing Directing Group for Ruthenium-Catalyzed C–H Activation/Annulation

European Journal of Organic Chemistry 2017
Elīna Līdumniece, Dace Rasiņa, Aigars Jirgensons

N-Sulfonylcarboxamides can act as both a directing group for C–H activation and an internal oxidant in the Ru-catalyzed annulation reaction with alkynes to give isoquinolones. Of all of the N-sulfonylcarboxamides that were studied, the N-(2,6-difluorophenyl)sulfonamide derivatives were found to be the most efficient and led to the formation of an unstable sulfinate byproduct that decomposed into 1,3-difluorobenzene under the reaction conditions. The described isoquinolone synthesis provides an alternative to the currently known traceless annulations of hydroxamic acid and sulfoximine derivatives.

Keywords
Ruthenium, C-H activation, N-sulfonylcarboxamide, oxidizing directing groups
DOI
10.1002/ejoc.201601582
Hyperlink
http://onlinelibrary.wiley.com/doi/10.1002/ejoc.201601582/full

Līdumniece, E., Rasiņa, D., Jirgensons, A. N-Sulfonylcarboxamide as an Oxidizing Directing Group for Ruthenium-Catalyzed C–H Activation/Annulation. European Journal of Organic Chemistry, 2017, Vol.2017, Iss.13, pp.1773-1779. e-ISSN 1099-0690. Available from: doi:10.1002/ejoc.201601582

Publication language
English (en)