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N ‐Sulfonylcarboxamide as an Oxidizing Directing Group for Ruthenium‐Catalyzed C–H Activation/Annulation
Author(s) -
Petrova Elina,
Rasina Dace,
Jirgensons Aigars
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201601582
Subject(s) - annulation , chemistry , oxidizing agent , ruthenium , sulfonamide , catalysis , hydroxamic acid , combinatorial chemistry , functional group , medicinal chemistry , group (periodic table) , stereochemistry , organic chemistry , polymer
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.