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三氟甲磺酸钪催化一锅多步串联反应法高效合成非对称 9-取代呫吨衍生物。

Scandium triflate-catalyzed one-pot domino approach towards general and efficient syntheses of unsymmetrical 9-substituted xanthene derivatives.

机构信息

Medicinal and Process Chemistry Division, Central Drug Research Institute, CSIR, Chattar Manzil Palace, Lucknow, 226001, UP, India.

出版信息

Org Biomol Chem. 2010 Mar 7;8(5):1097-105. doi: 10.1039/b919666h. Epub 2010 Jan 6.

Abstract

A general and efficient one-pot cascade/tandem approach to synthesize unsymmetrical 9-aryl/heteroaryl xanthenes has been developed under extremely mild reaction conditions using 10 mol% Sc(OTf)(3) as a catalyst. This strategy has been further extended to synthesize 9-(thioaryl) xanthenes through tandem carbon-sulfur (C-S) and carbon-carbon (C-C) bond formation. Novel C-C and C-S bond cleavage promoted by Sc(OTf)(3) is also discussed during mechanistic investigation.

摘要

一种通用且高效的一锅级联/串联方法,在极其温和的反应条件下,使用 10 mol% 的 Sc(OTf)(3)作为催化剂,合成了非对称 9-芳基/杂芳基呫吨。该策略进一步扩展到通过串联碳-硫 (C-S) 和碳-碳 (C-C) 键形成来合成 9-(硫代芳基)呫吨。在机理研究中还讨论了 Sc(OTf)(3)促进的新型 C-C 和 C-S 键断裂。

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