Hydroxylamine‐ O ‐Sulfonic Acid (HOSA) as a Redox‐Neutral Directing Group: Rhodium Catalyzed, Additive Free, One‐Pot Synthesis of Isoquinolines from Arylketones | Zendy

Biswal Pragati | Zendy; Pati Bedadyuti Vedvyas | Zendy; Chebolu Rajesh | Zendy; Ghosh Asit | Zendy; Ravikumar P. C. | Zendy

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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.

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