Literature DB >> 19681076

Hydrogen-deuterium exchange reactions of aromatic compounds and heterocycles by NaBD4-activated rhodium, platinum and palladium catalysts.

Volker Derdau1, Jens Atzrodt, Jochen Zimmermann, Carsten Kroll, Francois Brückner.   

Abstract

Conventional thermal and microwave conditions were compared for hydrogen-deuterium (H/D) exchange reactions of aminobenzoic acids catalysed by NaBD(4)-activated Pd/C or RhCl(3) with D(2)O as the deuterium source. We also investigated different NaBD(4)-activated metal catalysts (including Pd/C, RhCl(3) and Pt/C) under microwave conditions for an efficient H/D exchange of aromatic and heterocyclic compounds. Even higher deuterium incorporations were obtained for Pd/C and Pt/C catalyst mixtures due to the previously observed synergistic effect. Finally, we have applied these optimised conditions for one-step syntheses of the MS standards of several pharmaceutically active compounds.

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Year:  2009        PMID: 19681076     DOI: 10.1002/chem.200901107

Source DB:  PubMed          Journal:  Chemistry        ISSN: 0947-6539            Impact factor:   5.236


  9 in total

1.  Photoredox-catalyzed deuteration and tritiation of pharmaceutical compounds.

Authors:  Yong Yao Loh; Kazunori Nagao; Andrew J Hoover; David Hesk; Nelo R Rivera; Steven L Colletti; Ian W Davies; David W C MacMillan
Journal:  Science       Date:  2017-11-09       Impact factor: 47.728

2.  Flavin Metallaphotoredox Catalysis: Synergistic Synthesis in Water.

Authors:  Maheshwerreddy Chilamari; Jacob R Immel; Pei-Hsuan Chen; Bayan M Alghafli; Steven Bloom
Journal:  ACS Catal       Date:  2022-03-22       Impact factor: 13.700

3.  Formyl-selective deuteration of aldehydes with D2O via synergistic organic and photoredox catalysis.

Authors:  Jianyang Dong; Xiaochen Wang; Zhen Wang; Hongjian Song; Yuxiu Liu; Qingmin Wang
Journal:  Chem Sci       Date:  2019-12-04       Impact factor: 9.825

4.  Silver-catalyzed regioselective deuteration of (hetero)arenes and α-deuteration of 2-alkyl azaarenes.

Authors:  Baobiao Dong; Xuefeng Cong; Na Hao
Journal:  RSC Adv       Date:  2020-07-06       Impact factor: 3.361

5.  Isolation and identification of induced systemic resistance determinants from Bacillus simplex Sneb545 against Heterodera glycines.

Authors:  Zhifu Xing; Xiaojing Wu; Jing Zhao; Xuebing Zhao; Xiaofeng Zhu; Yuanyuan Wang; Haiyan Fan; Lijie Chen; Xiaoyu Liu; Yuxi Duan
Journal:  Sci Rep       Date:  2020-07-14       Impact factor: 4.379

6.  A Modified Arrhenius Approach to Thermodynamically Study Regioselectivity in Cytochrome P450-Catalyzed Substrate Conversion.

Authors:  Rosa A Luirink; Marlies C A Verkade-Vreeker; Jan N M Commandeur; Daan P Geerke
Journal:  Chembiochem       Date:  2020-02-25       Impact factor: 3.164

7.  Semiconductor photocatalysis to engineering deuterated N-alkyl pharmaceuticals enabled by synergistic activation of water and alkanols.

Authors:  Zhaofei Zhang; Chuntian Qiu; Yangsen Xu; Qing Han; Junwang Tang; Kian Ping Loh; Chenliang Su
Journal:  Nat Commun       Date:  2020-09-18       Impact factor: 14.919

8.  Controlled Tetradeuteration of Straight-Chain Fatty Acids: Synthesis, Application, and Insight into the Metabolism of Oxidized Linoleic Acid.

Authors:  Ayako Watanabe; Kotaro Hama; Kohei Watanabe; Yuko Fujiwara; Kazuaki Yokoyama; Shigeo Murata; Ryo Takita
Journal:  Angew Chem Int Ed Engl       Date:  2022-04-26       Impact factor: 16.823

9.  Palladium-Catalyzed Nondirected Late-Stage C-H Deuteration of Arenes.

Authors:  Mirxan Farizyan; Arup Mondal; Sourjya Mal; Fritz Deufel; Manuel van Gemmeren
Journal:  J Am Chem Soc       Date:  2021-09-28       Impact factor: 15.419

  9 in total

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