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Copper/ N,N,N′,N′ ‐Tetramethylethylenediamine‐Catalyzed Synthesis of N ‐Substituted Benzoheterocycles via CS Cross‐ Coupling at Ambient Temperature in Water
Author(s) -
Zhao Na,
Liu Liang,
Wang Fei,
Li Jia,
Zhang Wu
Publication year - 2014
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201400043
Subject(s) - chemistry , tetramethylethylenediamine , catalysis , copper , yield (engineering) , inert gas , tandem , inert , atmosphere (unit) , organic chemistry , combinatorial chemistry , metallurgy , meteorology , materials science , physics , composite material
Copper/ N,N,N′,N′ ‐tetramethylethylenediamine (Cu/TMEDA)‐catalyzed ambient temperature tandem reactions of isothiocyanates with 2‐iodophenols or 2‐iodoanilines in water without the protection of an inert atmosphere are described, which provide a simple, rapid, environmental method for the synthesis of a variety of 2‐iminobenzo‐1, 3‐ oxathioles and 2‐aminobenzothiazoles in good yields. More important, the present reaction process needs only low amounts of copper catalyst (<1 mol%) and can yield the products on a gram scale.