Volume 2017, Issue 13 p. 1773-1779
Full Paper

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

Elina Petrova

Elina Petrova

Latvian Institute of Organic Synthesis, Aizkraukles 21, 1006 Riga, Latvia

Search for more papers by this author
Dace Rasina

Dace Rasina

Latvian Institute of Organic Synthesis, Aizkraukles 21, 1006 Riga, Latvia

Search for more papers by this author
Aigars Jirgensons

Corresponding Author

Aigars Jirgensons

Latvian Institute of Organic Synthesis, Aizkraukles 21, 1006 Riga, Latvia

Latvian Institute of Organic Synthesis, Aizkraukles 21, Riga 1006, Latvia

E-mail: [email protected]

http://osmg.osi.lv/

Search for more papers by this author
First published: 06 February 2017
Citations: 25

Graphical Abstract

N-Sulfonylcarboxamides can act as a directing group for C–H activation and an internal oxidant in the Ru-catalyzed annulation with alkynes to give isoquinolones. The N-(2,6-difluorophenyl)sulfonamides were the most efficient of the examined N-sulfonylcarboxamides and led to the formation of an unstable sulfinate byproduct that decomposed into 1,3-difluorobenzene under the reaction conditions. DG = directing group.

Abstract

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.