Gold Catalyzed [3+2] Oxidative Annulation of 1,3‐Enyne with Indole

IF 2.8 4区 化学 Q1 CHEMISTRY, ORGANIC Asian Journal of Organic Chemistry Pub Date : 2024-09-03 DOI:10.1002/ajoc.202400356
Zili Chen, Qiang Zou, Yu-Jiang Wang, Ya-Ru Wan
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Abstract

An efficient new method has been developed for the synthesis of ketone‐integrated cyclopentene‐fused indoline derivatives with a high regioselectivity through gold‐catalyzed oxidative cyclo‐coupling of 1,3‐enynes with indoles by using 2,6‐dichloropyridine N‐oxide as the terminal oxidant. A plausible mechanism has been proposed, in which, a cascade process of nucleophilic trapping of the vinyl gold carbene surrogate with indole followed by the subsequent intramolecular cyclization provides the dearomative formal [3+2] cycloaddition product. In addition, a scale‐up reaction and further derivation via cyclopentene’s epoxidation & hydrazone derivative’s 1,5‐ electrocyclization have been performed.
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金催化 1,3-炔与吲哚的 [3+2] 氧化环化反应
以 2,6-二氯吡啶 N-氧化物为末端氧化剂,通过金催化 1,3-enynes 与吲哚的氧化环偶联反应,开发出一种高效的新方法,用于合成具有高区域选择性的酮集成环戊烯融合吲哚啉衍生物。在这一过程中,吲哚与乙烯基碳金代用品发生亲核捕获的级联反应,随后发生分子内环化反应,从而生成脱芳作用的正式 [3+2] 环加成产物。此外,还进行了放大反应,并通过环戊烯的环氧化& 酰腙衍生物的 1,5- 电环化进一步衍生。
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来源期刊
CiteScore
4.70
自引率
3.70%
发文量
372
期刊介绍: Organic chemistry is the fundamental science that stands at the heart of chemistry, biology, and materials science. Research in these areas is vigorous and truly international, with three major regions making almost equal contributions: America, Europe and Asia. Asia now has its own top international organic chemistry journal—the Asian Journal of Organic Chemistry (AsianJOC) The AsianJOC is designed to be a top-ranked international research journal and publishes primary research as well as critical secondary information from authors across the world. The journal covers organic chemistry in its entirety. Authors and readers come from academia, the chemical industry, and government laboratories.
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