Accessing Highly Substituted Indoles via B(C 6 F 5 ) 3 -Catalyzed Secondary Alkyl Group Transfer

Accessing Highly Substituted Indoles via B(C 6 F 5 ) 3 -Catalyzed Secondary Alkyl Group Transfer
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通过 B(C 6 F 5 ) 3 催化仲烷基转移获得高度取代的吲哚

DOI:
10.1021/acs.joc.4c00025
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发表时间:
2024
期刊:
The Journal of Organic Chemistry
影响因子:
--
通讯作者:
Elsherbeni S
Elsherbeni S
中科院分区:
--
文献类型:
--
作者:
Elsherbeni S

文献摘要

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在此,我们报告了一种通过B(C6F5)3催化从胺中转移2°烷基来获得一系列高取代吲哚的合成方法。无过渡金属的催化方法已被证明适用于广泛的吲哚和胺2°烷基供体,包括两种反应组分上的各种取代基,以获得有用的C(3)-烷基化吲哚产物。烷基转移过程可以使用Schlenk线技术与市售的B(C6F5)3·nH2O和溶剂相结合进行,从而避免了对专用设备(例如手套箱)的要求。
Herein, we report a synthetic method to access a range of highly substituted indoles via the B(C6F5)3-catalyzed transfer of 2° alkyl groups from amines. The transition-metal-free catalytic approach has been demonstrated across a broad range of indoles and amine 2° alkyl donors, including various substituents on both reacting components, to access useful C(3)-alkylated indole products. The alkyl transfer process can be performed using Schlenk line techniques in combination with commercially available B(C6F5)3·nH2O and solvents, which obviates the requirement for specialized equipment (e.g., glovebox).