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Copper-Catalyzed [3 + 2] Annulation of O-Acyl Oximes with 4-Sulfonamidophenols for the Synthesis of 5-Sulfonamidoindoles and 2-Amido-5-sulfonamidobenzofuran-3(2H)-ones
Organic Letters ( IF 5.2 ) Pub Date : 2024-05-13 , DOI: 10.1021/acs.orglett.4c01071
Zi-Jun Hu 1 , Wei Chen 2 , Xinyu Lyu 1 , Hui-Peng Zhang 1 , Si-Wei Chen 1 , Xian-Heng Ding 1 , Cang-Hai Yu 1 , Zhen Cui 1 , Chun-Bao Miao 1 , Hai-Tao Yang 1
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A copper-catalyzed [3 + 2] annulation of O-acyl oximes with 4-sulfonamidophenols is developed. The advantage of this method lies in the concurrent double activation of two substrates to form nucleophilic enamines and electrophilic quinone monoimines. The substituent on the α-carbon of O-acyl oxime determines two different reaction pathways, thereby leading to the selective generation of 5-sulfonamidoindoles and 2-amido-5-sulfonamidobenzofuran-3(2H)-ones.

中文翻译:


铜催化 O-酰基肟与 4-磺酰胺基苯酚的 [3 + 2] 环化反应合成 5-磺酰胺基吲哚和 2-酰胺基-5-磺酰胺基苯并呋喃-3(2H)-酮



开发了铜催化的 O-酰基肟与 4-磺酰胺苯酚的 [3 + 2] 成环反应。该方法的优点在于同时双重活化两种底物,形成亲核烯胺和亲电醌单亚胺。 O-酰基肟的α-碳上的取代基决定了两种不同的反应途径,从而导致5-磺酰胺吲哚和2-酰胺基-5-磺酰胺苯并呋喃-3(2H)-酮的选择性生成。
更新日期:2024-05-13
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