Palladium-catalyzed ortho-selective C–H hydroxylation of carboxybenzyl-protected benzylamines

Chenyang Dai; Yi Han; Lingling Liu; Zhi-Bin Huang; Da-Qing Shi; Yingsheng Zhao

doi:10.1039/C9QO01523J

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Palladium-catalyzed ortho-selective C–H hydroxylation of carboxybenzyl-protected benzylamines†

Chenyang Dai,^a Yi Han,^a Lingling Liu,^a Zhi-Bin Huang,^a Da-Qing Shi

*^a and Yingsheng Zhao

*^a

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* Corresponding authors

^a Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, China
E-mail: dqshi@suda.edu.cn, yszhao@suda.edu.cn

Abstract

A convenient approach to synthesize o-hydroxybenzylamine via Pd-catalyzed hydroxylation of benzylamine with a removable Cbz-amide as the directing group was developed. Various functional groups were well tolerated, leading to various substituted o-hydroxybenzylamines in moderate to good yields.

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Article information

DOI: https://doi.org/10.1039/C9QO01523J
Article type: Research Article
Submitted: 23 Dec 2019
Accepted: 01 Jun 2020
First published: 02 Jun 2020

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Org. Chem. Front., 2020,7, 1703-1708

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Palladium-catalyzed ortho-selective C–H hydroxylation of carboxybenzyl-protected benzylamines

C. Dai, Y. Han, L. Liu, Z. Huang, D. Shi and Y. Zhao, Org. Chem. Front., 2020, 7, 1703 DOI: 10.1039/C9QO01523J

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Palladium-catalyzed ortho-selective C–H hydroxylation of carboxybenzyl-protected benzylamines†

Abstract

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Palladium-catalyzed ortho-selective C–H hydroxylation of carboxybenzyl-protected benzylamines

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