Triazole‐Assisted Ruthenium‐Catalyzed CH Arylation of Aromatic Amides |
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| Authors: | Dr Hamad H Al Mamari Dr Emelyne Diers Prof Dr Lutz Ackermann |
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| Affiliation: | Institut für Organische und Biomolekulare Chemie, Georg‐August‐Universit?t, Tammannstrasse 2, 37077 G?ttingen (Germany), Fax: (+49)?551‐39‐6777 |
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| Abstract: | Site‐selective ruthenium(II)‐catalyzed direct arylation of amides was achieved through C?H cleavages with modular auxiliaries, derived from easily accessible 1,2,3‐triazoles. The triazolyldimethylmethyl (TAM) bidentate directing group was prepared in a highly modular fashion through copper(I)‐catalyzed 1,3‐dipolar cycloaddition and allowed for ruthenium‐catalyzed C?H arylations on arenes and heteroarenes, as well as alkenes, by using easy‐to‐handle aryl bromides as the arylating reagents. The triazole‐assisted C?H activation strategy was found to be widely applicable, to occur under mild reaction conditions, and the catalytic system was tolerant of important electrophilic functionalities. Notably, the flexible triazole‐based auxiliary proved to be a more potent directing group for the optimized ruthenium(II)‐catalyzed direct arylations, compared with pyridyl‐substituted amides or substrates derived from 8‐aminoquinoline. |
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| Keywords: | amides aryl halides catalysis C H activation ruthenium triazoles |
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