瞬时指导基团催化吲哚的 C4 选择性炔化反应

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2024-08-06 DOI:10.1021/acs.orglett.4c0197010.1021/acs.orglett.4c01970

Ze-Xuan Zhang, Bing Zhang, Meng Yuan, Peng-Fei Zhao and Chao-Shan Da*,

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引用次数: 0

摘要

以丙氨酸为瞬时指导基团，在钯催化下成功地在吲哚 C4 位进行了区域选择性炔化反应，并取得了良好的收率。PAF 拮抗剂的全合成证明了这一合成方案的实用性。催化过程中制备的 C4 选择性帕拉代环中间体以及对吲哚的 C4 位和 C2 位选择性 C-H 活化能垒的 DFT 计算明确证明了其区域选择性。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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

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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 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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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.