Selective Cyclization of Arylnitrones to Indolines under External Oxidant-Free Conditions: Dual Role of Rh(III) Catalyst in the C-H Activation and Oxygen Atom Transfer

Selective Cyclization of Arylnitrones to Indolines under External Oxidant-Free Conditions: Dual Role of Rh(III) Catalyst in the C-H Activation and Oxygen Atom Transfer
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DOI:
10.1021/jacs.5b01065
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发表时间:
2015-04-22
影响因子:
15
通讯作者:
Chang, Sukbok
Chang, Sukbok
中科院分区:
化学1区
文献类型:
--
作者:
Dateer, Ramesh B.;Chang, Sukbok

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提出了在无外部氧化剂条件下 Rh(III) 催化芳基硝酮环化为二氢吲哚的第一个例子。 Cp*Rh(III) 催化剂介导 C-H 键活化和 O 原子转移的双重作用使得芳基硝酮与内部炔烃的分子间偶联成为可能。以良好的产率和高非对映选择性获得了合成上重要且具有药理学优势的二氢吲哚衍生物。
The first example of Rh(III)-catalyzed cyclization of arylnitrones to indolines under external oxidant-free conditions is presented. An intermolecular coupling of arylnitrones with internal alkynes is made possible by the dual role of the Cp*Rh(III) catalyst mediating both the C-H bond activation and O-atom transfer. Synthetically important and pharmacologically privileged indoline derivatives were obtained in good yields with high diastereoselectivity.