Direct ortho-Selective C–H Functionalization of Carboxybenzyl-Protected Arylalkylamines via Ir(III)-Catalyzed C–H Activation

A convenient and practical approach to synthesize ortho-alkynylated arylalkylamines through ortho-selective C–H functionalization has been developed using Cbz-amide as the directing group and Ir­(III) as the catalyst. Various substrates were well tolerated, affording the corresponding products in mo...

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Bibliographic Details
Published in:Organic letters 2018-04, Vol.20 (8), p.2454-2458
Main Authors: Li, Guobao, Hu, Jundie, Zeng, Runsheng, Shi, Da-Qing, Zhao, Yingsheng
Format: Article
Language:English
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Summary:A convenient and practical approach to synthesize ortho-alkynylated arylalkylamines through ortho-selective C–H functionalization has been developed using Cbz-amide as the directing group and Ir­(III) as the catalyst. Various substrates were well tolerated, affording the corresponding products in moderate to good yields. Moreover, preliminary mechanistic study revealed the role of the amide as the coordination center to cooperate with the Ir­(III) complex during C–H activation. Development of this Cbz-amide-promoted CAr–H functionalization offers a practical approach with potential applications in organic synthesis.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.8b00797