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TBHP Mediated Substrate Controlled Oxidative Dearomatization of Indoles to C2/C3‐Quaternary Indolinones
Author(s) -
Kothandapani Jagatheeswaran,
Reddy Singarajanahalli Mundarinti Krishna,
Thamotharan Subbiah,
Kumar Shankar Madan,
Byrappa Kullaiah,
Ganesan Subramaniapillai Selva
Publication year - 2018
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.201800167
Subject(s) - chemistry , isatin , indole test , substituent , quaternary carbon , substrate (aquarium) , organic chemistry , enantioselective synthesis , catalysis , oceanography , geology
Oxidative dearomatization of indoles with 70 % aqueous tert ‐butylhydroperoxide (TBHP) in the absence of any metal salts/organic solvents gave the corresponding C2/C3‐quaternary indolinones under open‐air reaction conditions. The nature of substituent on the indole nitrogen dictates the type of product formed in these reactions. Free (NH)‐indoles gave C2‐quaternary indolinone derivatives whilst (NR)‐indoles yielded C3‐quaternary indolinones as the major product. Moreover, the addition of an excess amount of TBHP also facilitated the one‐pot transformation of (NR)‐indoles to the corresponding isatin derivatives.