3-Sulfonylindoles via Gold- or Silver-Catalyzed Cyclization─1,3-Sulfonyl Migration Sequences under Visible Light Irradiation

IF 3.3 Q2 CHEMISTRY, MULTIDISCIPLINARY

ACS Organic & Inorganic Au Pub Date : 2022-09-28 DOI:10.1021/acsorginorgau.2c00034

Fen Zhao, Wided Hagui, María Ballarín-Marión, Cyril Ollivier*, Virginie Mouriès-Mansuy* and Louis Fensterbank*,

引用次数: 1

Abstract

A pathway for the synthesis of 3-sulfonylindoles has been devised. Upon blue LED irradiation, in the presence of a gold(I) or a silver(I) salt, ortho-alkynyl N-sulfonyl precursors readily undergo a 5-endo-dig cyclization concomitant with a 1,3-sulfonyl migration. While the gold-catalyzed reaction takes place in photocatalyst-free conditions, an iridium photocatalyst (Ir[dF(CF₃)ppy]₂(dtbbpy)PF₆) is necessary with silver catalysis. Mechanistic studies featuring the generation of a sulfonyl radical support this dichotomy.

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金或银催化环化的3-磺酰基吲哚─1,3-磺酰基在可见光照射下的迁移序列

已经设计了一种合成3-磺酰基吲哚的途径。在蓝色LED照射下，在金（I）或银盐（I）的存在下，邻炔基N-磺酰基前体容易经历伴随1，3-磺酰基迁移的5-内二醇环化。虽然金催化的反应发生在无光催化剂的条件下，但铱光催化剂（Ir[dF（CF3）ppy]2（dtbbpy）PF6）在银催化下是必要的。以磺酰基自由基生成为特征的机制研究支持这种二分法。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

ACS Organic & Inorganic Au 有机化学、无机化学-

CiteScore

4.10

自引率

0.00%

发文量

期刊介绍： ACS Organic & Inorganic Au is an open access journal that publishes original experimental and theoretical/computational studies on organic organometallic inorganic crystal growth and engineering and organic process chemistry. Short letters comprehensive articles reviews and perspectives are welcome on topics that include:Organic chemistry Organometallic chemistry Inorganic Chemistry and Organic Process Chemistry.