One-Pot, Two-Step Reductive Amination of Boronate Ester Containing Aromatic Amines and Aldehydes Using B2pin2 as Reductant

doi:10.6023/cjoc201902011

Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (7): 2001-2008.DOI: 10.6023/cjoc201902011 Previous Articles Next Articles

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B₂pin₂参与的含硼酸酯的芳香胺和醛的一锅两步还原胺化反应

刘雪滢^a, 刘振伟^a, 郭圆圆^a, 李敬亚^b, 邹大鹏^a, 吴豫生^b, 吴养洁^a

a 郑州大学化学与分子工程学院郑州 450052;
b 郑州泰基鸿诺医药股份有限公司郑州 450052

收稿日期:2019-02-13 修回日期:2019-03-15 发布日期:2019-03-29
通讯作者: 邹大鹏, 吴豫生, 吴养洁 E-mail:yusheng.wu@tetranovglobal.com;wyj@zzu.edu.cn;zdp@zzu.edu.cn
基金资助:
国家自然科学基金（Nos.21172200，21702191）资助项目.

One-Pot, Two-Step Reductive Amination of Boronate Ester Containing Aromatic Amines and Aldehydes Using B₂pin₂ as Reductant

Liu Xueying^a, Liu Zhenwei^a, Guo Yuanyuan^a, Li Jingya^b, Zou Dapeng^a, Wu Yusheng^b, Wu Yangjie^a

a College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou 450052;
b Tetranov Biopharm, Limited Liability Company, Zhengzhou 450052

Received:2019-02-13 Revised:2019-03-15 Published:2019-03-29
Contact: 10.6023/cjoc201902011 E-mail:yusheng.wu@tetranovglobal.com;wyj@zzu.edu.cn;zdp@zzu.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21172200, 21702191).

1. One-Pot, Two-Step Reductive Amination of Boronate Ester Containing Aromatic Amines and Aldehydes Using B₂pin₂ as Reductant.PDF(2872KB)

Abstract

The aromatic amine functionality occupies a very important role in organic chemistry due to its prominence in biological and naturally occurring molecules. In addition, the synthesized secondary aromatic amines with pendant boronate ester are versatile intermediates in several organic transformations. The one-pot, two-step reductive amination of boron-containing primary aromatic amines and aldehydes has been achieved in the presence of NaOH in ethanol using B₂pin₂ as reductant. After extensive screening of various reaction parameters, such as base, reaction temperature, solvent, reaction time and protective gas, a series of secondary aromatic amines with pendant boronate ester and various functional groups were obtained in moderate to good yields under the optimal reaction conditions. This system features generally high yields and broad functional group tolerance. The boronate ester substituent is a very good handle to be further functionalized.

Key words: reductive amination, boron-containing secondary aromatic amines, bis (pinacolato) diboron, aldehydes

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Liu Xueying, Liu Zhenwei, Guo Yuanyuan, Li Jingya, Zou Dapeng, Wu Yusheng, Wu Yangjie. One-Pot, Two-Step Reductive Amination of Boronate Ester Containing Aromatic Amines and Aldehydes Using B₂pin₂ as Reductant[J]. Chin. J. Org. Chem., 2019, 39(7): 2001-2008.

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B₂pin₂参与的含硼酸酯的芳香胺和醛的一锅两步还原胺化反应

One-Pot, Two-Step Reductive Amination of Boronate Ester Containing Aromatic Amines and Aldehydes Using B₂pin₂ as Reductant

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B2pin2参与的含硼酸酯的芳香胺和醛的一锅两步还原胺化反应