Divergent Annulative C–C Coupling of Indoles Initiated by Manganese-Catalyzed C–H Activation

Manganese­(I)-catalyzed C–H activation of indoles and divergent annulative coupling with alkyne-tethered cyclohexadienones has been realized under operationally simple conditions. These annulation systems are under condition control. The coupling in the presence of BPh3 additive followed a C–H activ...

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Bibliographic Details
Published in:ACS catalysis 2018-10, Vol.8 (10), p.9463-9470
Main Authors: Liu, Bingxian, Li, Jie, Hu, Panjie, Zhou, Xukai, Bai, Dachang, Li, Xingwei
Format: Article
Language:English
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Summary:Manganese­(I)-catalyzed C–H activation of indoles and divergent annulative coupling with alkyne-tethered cyclohexadienones has been realized under operationally simple conditions. These annulation systems are under condition control. The coupling in the presence of BPh3 additive followed a C–H activation-alkyne insertion-Michael addition pathway, affording an exocyclic olefin attached to a tetrahydrofuran ring. In contrast, when Zn­(OAc)2/PivOH additives were introduced, initial olefination en route to intramolecular Diels–Alder reaction and subsequent elimination of an alcohol was followed to deliver a fused six-membered ring. The selectivity stands in contrast to those reported using rhodium­(III) and cobalt­(III) catalysts, highlighting the unique reactivity and selectivity of manganese catalysts.
ISSN:2155-5435
2155-5435
DOI:10.1021/acscatal.8b02560