Ru(II)-Catalyzed C7 Trifluoromethylthiolation and Thioarylation of Indolines Using Bench-Stable Reagents

被引：1

作者：

Sumit, Devesh ^{[1
]}

Sachin, Upendra ^{[1
,2
]}

Chandra, Devesh ^{[1
]}

Sharma, Upendra ^{[1
,2
]}

机构：

[1] CSIR IHBT, Chem Technol Div, C H Activat & Phytochem Lab, Palampur 176061, India

[2] Acad Sci & Innovat Res AcSIR, Ghaziabad 201002, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 89卷 / 21期

关键词：

BOND FORMATION;

D O I：

10.1021/acs.joc.4c02058

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A Ru(II)-catalyzed C(sp2)-H trifluoromethylthiolation and thioarylation of indolines using bench-stable reagents have been explored. Diversely substituted indolines were functionalized at C7 position in good to excellent yields. Radical quenching, deuterium labeling, KIE, and reaction order determination experiments were performed to support the proposed reaction pathway. Gram-scale synthesis and post-transformation of the synthesized products have also been carried out to demonstrate the applicability of the developed catalytic protocol.

引用

页码：15893 / 15900

页数：8

共 44 条

[1] Ru(II)-catalyzed regioselective C-7 hydroxymethylation of indolines with formaldehyde
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[3] Rhodium-Catalyzed Direct C7 Alkynylation of Indolines
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[4] Rh(III)-Catalyzed Selective C7 Halogenation of Indolines
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[6] Pd-Catalyzed Direct C7 Trifluoromethylation of Indolines with Umemoto's Reagent
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[7] Rhodium(III)- and Iridium(III)-Catalyzed C7 Alkylation of Indolines with Diazo Compounds
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[8] Synthesis of bench-stable solid triorganoindium reagents and reactivity in palladium-catalyzed cross-coupling reactions
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[9] Bench-Stable Electrophilic Indole and Pyrrole Reagents: Serendipitous Discovery and Use in C-H Functionalization
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[10] Oxidative Palladium(II)-Catalyzed C-7 Alkenylation of Indolines
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