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Direct Access to Halogenated Fused Imidazo[1,5‐ a ] N ‐heteroaromatics through Copper‐Promoted Double Oxidative C–H Amination and Halogenation
Author(s) -
Sandeep Mummadi,
Swati Dushyant Patil,
Sravani Boda,
Rajender Reddy Kallu
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.201800628
Subject(s) - chemistry , amination , halogenation , halogen , copper , yield (engineering) , catalysis , oxidative phosphorylation , combinatorial chemistry , functional group , organic chemistry , oxidative coupling of methane , coupling reaction , medicinal chemistry , biochemistry , alkyl , materials science , polymer , metallurgy
An aerobic copper‐promoted double oxidative C–H amination and halogenation tandem reaction of 2‐methylazarenes with aliphatic amines or amino acids has been developed. The reaction uses copper salts as catalysts as well as halogen sources, and molecular oxygen as the sole oxidant. This protocol is operationally simple, and gives direct access to functionalised fused imidazoles in a one‐pot operation with good functional‐group tolerance. The synthetic utility of the products has been tested in a Suzuki cross‐coupling reaction, which proceeded in good yield.