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...

Full description

Saved in:
Bibliographic Details
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
Format: Article
Language:English
Citations: Items that this one cites
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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.
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.4c01970