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Hydroxylamine‐ O ‐Sulfonic Acid (HOSA) as a Redox‐Neutral Directing Group: Rhodium Catalyzed, Additive Free, One‐Pot Synthesis of Isoquinolines from Arylketones
Author(s) -
Biswal Pragati,
Pati Bedadyuti Vedvyas,
Chebolu Rajesh,
Ghosh Asit,
Ravikumar P. C.
Publication year - 2020
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.201901825
Subject(s) - chemistry , hydroxylamine , rhodium , sulfonic acid , catalysis , annulation , redox , organic chemistry , base (topology) , functional group , metal , medicinal chemistry , polymer chemistry , mathematical analysis , polymer , mathematics
A new application of hydroxylamine‐ O ‐sulfonic acid (HOSA) has been discovered whereby aromatic ketones react with HOSA and alkynes to form isoquinolines in the presence of a Rh III catalyst. This C–H/N–O annulation methodology gives excellent yields even without any silver additive, acid/base or metal oxidant. This is the first report wherein a directing group is simultaneously forming in situ, acting as acid additive, and also as an internal oxidant.