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Metal‐Free, One‐Pot Oxidative Triple Functionalization of Azaarenes with Methyl Arenes Mediated by Molecular Iodine/TBHP: Synthesis of N‐Benzylated Iodo(iso)quinolinones
Author(s) -
Shantharjun Bangarigalla,
Rajeswari Radhakrishnan,
Vani Damera,
Unnava Ramanjaneyulu,
Sridhar Balasubramanian,
Reddy Kallu Rajender
Publication year - 2019
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201900588
Subject(s) - chemistry , sonogashira coupling , surface modification , regioselectivity , iodine , halogenation , combinatorial chemistry , catalysis , palladium , organic chemistry , triple bond , double bond
An efficient metal‐free one‐pot triple functionalization of azaarenes has been developed via a successive regioselective iodination, N‐ benzylation and amidation by using readily available methylarenes in presence of molecular iodine and TBHP. This method avoids the use of expensive noble metal catalysts and multi‐step conversions. Moreover, we have shown the synthetic utility of the iodo functionality with traditional cross‐coupling reactions (like Suzuki, Heck and Sonogashira) and the corresponding products were obtained in good yields.