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Divergent Coupling of Anilines and Enones by Integration of C−H Activation and Transfer Hydrogenation
Author(s) -
Zhou Xukai,
Xia Jintao,
Zheng Guangfan,
Kong Lingheng,
Li Xingwei
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201803347
Subject(s) - disproportionation , iridium , hydride , transfer hydrogenation , chemistry , catalysis , coupling (piping) , redox , coupling reaction , combinatorial chemistry , photochemistry , organic chemistry , hydrogen , materials science , ruthenium , metallurgy
Cp*Rh III /Ir III complexes are known to play important roles in both C−H activation and transfer hydrogenation (TH). However, these two areas evolved separately. They have been integrated in redox‐ and chemodivergent coupling reactions of N ‐pyridylanilines with enones. The iridium‐catalyzed coupling with enones leads to the efficient synthesis of tetrahydroquinolines through TH from i PrOH. Counterintuitively, i PrOH does not serve as the sole hydride source, and the major reaction pathway involves disproportionation of a dihydroquinoline intermediate, followed by the convergent and iterative reduction of quinolinium species.