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Rhodium(III)‐Catalyzed One‐Pot Access to Isoquinolines and Heterocycle‐Fused Pyridines in Aqueous Medium through C–H Cleavage
Author(s) -
Zhang Jitan,
Qian Hongsheng,
Liu Zhanxiang,
Xiong Chunhua,
Zhang Yuhong
Publication year - 2014
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.201403085
Subject(s) - chemistry , catalysis , rhodium , annulation , ammonium acetate , aqueous medium , aqueous solution , bond cleavage , aryl , environmentally friendly , combinatorial chemistry , organic chemistry , medicinal chemistry , ecology , alkyl , high performance liquid chromatography , biology
An efficient Rh III ‐catalyzed ortho ‐C–H bond activation for the synthesis of substituted isoquinolines and heterocycle‐fused pyridines in aqueous medium has been developed. This method involves the in situ generation of ketimines from ketones and ammonium acetate and subsequent oxidative C–H bond activation/annulation of ketimines with alkynes to form the C–C/C–N bonds spontaneously. Various aryl ketones and internal alkynes were smoothly transformed into the desired heterocycles in moderate to excellent yields. The reaction exploits molecular oxygen as the sole oxidant by producing water as the only byproduct. Moreover, easily available NH 4 OAc was utilized as the nitrogen source, which makes this protocol practical and environmentally friendly.