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通过钯催化三甲铵盐与芳基硼酸的铃木耦合反应合成三芳基甲烷

Synthesis of Triarylmethanes via Palladium-Catalyzed Suzuki Coupling of Trimethylammonium Salts and Arylboronic Acids.

作者信息

Zhang Zhenming, Wang Hui, Qiu Nianli, Kong Yujing, Zeng Wenjuan, Zhang Yongquan, Zhao Junfeng

机构信息

Key Laboratory of Chemical Biology of Jiangxi Province, College of Chemistry and Chemical Engineering , Jiangxi Normal University , Nanchang 330022 , P.R. China.

出版信息

J Org Chem. 2018 Aug 3;83(15):8710-8715. doi: 10.1021/acs.joc.8b00965. Epub 2018 Jul 18.

DOI:10.1021/acs.joc.8b00965
PMID:29978707
Abstract

An efficient palladium-catalyzed Suzuki coupling of 1,1-diarylmethyl-trimethylammonium triflates with arylboronic acids is reported. This reaction offers a novel approach to triarylmethane derivatives in good to excellent yields with the palladium-catalyzed C-N bond cleavage as the key feature. Broad substrate scope regarding both reaction partners are observed. Moreover, reactive functional groups such as vinyl and formyl groups are conserved in this transformation.

摘要

据报道,钯催化1,1 - 二芳基甲基三氟甲磺酸三甲铵与芳基硼酸进行高效的铃木偶联反应。该反应提供了一种制备三芳基甲烷衍生物的新方法,产率良好至优异,其关键特征是钯催化的C-N键裂解。观察到两种反应底物都具有广泛的底物范围。此外,乙烯基和甲酰基等活性官能团在该转化过程中得以保留。

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引用本文的文献

1
Synthesis of Triarylmethanes via Palladium-Catalyzed Suzuki-Miyaura Reactions of Diarylmethyl Esters.通过二芳基甲基酯的钯催化铃木-宫浦反应合成三芳基甲烷
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2
Triarylmethanes and their Medium-Ring Analogues by Unactivated Truce-Smiles Rearrangement of Benzanilides.未活化的 Truce-Smiles 重排反应在苯甲酰苯胺上构建三芳基甲烷及其中环类似物。
Angew Chem Int Ed Engl. 2021 May 10;60(20):11272-11277. doi: 10.1002/anie.202102192. Epub 2021 Apr 8.
3
Transition-Metal-Free Synthesis of Polyfunctional Triarylmethanes and 1,1-Diarylalkanes by Sequential Cross-Coupling of Benzal Diacetates with Organozinc Reagents.
无过渡金属条件下通过苯偶姻二乙酸酯与有机锌试剂的串联交叉偶联反应合成多功能三芳基甲烷和 1,1-二芳基烷烃。
Angew Chem Int Ed Engl. 2021 Apr 26;60(18):10409-10414. doi: 10.1002/anie.202101682. Epub 2021 Mar 17.