Pd(II)-Catalyzed C4-Selective Alkynylation of Indoles by a Transient Directing Group

With alanine as a transient directing group, Pd-catalyzed regioselective alkynylation at the indole C4-position was successfully established in a good yield. The total synthesis of the PAF antagonist demonstrated the synthetic utility of this protocol. The regioselectivity was explicitly proven by t...

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Published in:Organic letters 2024-08, Vol.26 (32), p.6819-6824
Main Authors: Zhang, Ze-Xuan, Zhang, Bing, Yuan, Meng, Zhao, Peng-Fei, Da, Chao-Shan
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Language:English
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container_end_page 6824
container_issue 32
container_start_page 6819
container_title Organic letters
container_volume 26
creator Zhang, Ze-Xuan
Zhang, Bing
Yuan, Meng
Zhao, Peng-Fei
Da, Chao-Shan
description With alanine as a transient directing group, Pd-catalyzed regioselective alkynylation at the indole C4-position was successfully established in a good yield. The total synthesis of the PAF antagonist demonstrated the synthetic utility of this protocol. The regioselectivity was explicitly proven by the prepared C4-selective palladacycle intermediate in the catalytic process and the DFT calculation of the energy barriers of C4- and C2-site-selective C–H activation of indole.
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title Pd(II)-Catalyzed C4-Selective Alkynylation of Indoles by a Transient Directing Group
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