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Literature DB >> 32256276

B(C₆F₅)₃-Catalyzed α-Deuteration of Bioactive Carbonyl Compounds with D₂O.

Yejin Chang¹, Tanner Myers¹, Masayuki Wasa¹.

Abstract

An efficient deuteration process of α-C-H bonds in various carbonyl-based pharmaceutical compounds has been developed. Catalytic reactions are initiated by the action of Lewis acidic B(C6F5)3 and D2O, converting a drug molecule into the corresponding boron-enolate. Ensuing deuteration of the enolate by in situ-generated D2O+-H then results in the formation of α-deuterated bioactive carbonyl compounds with up to >98% deuterium incorporation.

Entities: Chemical Disease

Keywords: Cooperative catalysis; Deuterated drug; Frustrated Lewis pair; Late-stage functionalization

Year: 2019 PMID： 32256276 PMCID： PMC7108789 DOI： 10.1002/adsc.201901419

Source DB: PubMed Journal: Adv Synth Catal ISSN： 1615-4150 Impact factor: 5.837

34 in total

1. Ruthenium-catalyzed selective α,β-deuteration of bioactive amines.

Authors: Lorenz Neubert; Dirk Michalik; Sebastian Bähn; Sebastian Imm; Helfried Neumann; Jens Atzrodt; Volker Derdau; Wolfgang Holla; Matthias Beller
Journal: J Am Chem Soc Date: 2012-07-12 Impact factor: 15.419

2. Triazabicyclodecene: an effective isotope exchange catalyst in CDCl(3).

Authors: Cyrille Sabot; Kanduluru Ananda Kumar; Cyril Antheaume; Charles Mioskowski
Journal: J Org Chem Date: 2007-05-27 Impact factor: 4.354

3. Frustrated Lewis pair chemistry: development and perspectives.

Authors: Douglas W Stephan; Gerhard Erker
Journal: Angew Chem Int Ed Engl Date: 2015-05-14 Impact factor: 15.336

4. A simple method for α-position deuterated carbonyl compounds with pyrrolidine as catalyst.

Authors: Miao Zhan; Tao Zhang; Haoxi Huang; Yongmei Xie; Yuanwei Chen
Journal: J Labelled Comp Radiopharm Date: 2014-07-03 Impact factor: 1.921

5. 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

6. Highly efficient redox isomerization of allylic alcohols at ambient temperature catalyzed by novel ruthenium-cyclopentadienyl complexes--new insight into the mechanism.

Authors: Belén Martín-Matute; Krisztián Bogár; Michaela Edin; F Betül Kaynak; Jan-E Bäckvall
Journal: Chemistry Date: 2005-10-07 Impact factor: 5.236

B(C₆F₅)₃-Catalyzed α-Deuteration of Bioactive Carbonyl Compounds with D₂O.

1. Ruthenium-catalyzed selective α,β-deuteration of bioactive amines.

2. Triazabicyclodecene: an effective isotope exchange catalyst in CDCl(3).

3. Frustrated Lewis pair chemistry: development and perspectives.

4. A simple method for α-position deuterated carbonyl compounds with pyrrolidine as catalyst.

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

6. Highly efficient redox isomerization of allylic alcohols at ambient temperature catalyzed by novel ruthenium-cyclopentadienyl complexes--new insight into the mechanism.

7. Asymmetric organic catalysis with modified cinchona alkaloids.

8. FLP-mediated activations and reductions of CO2 and CO.

9. Iron-catalysed tritiation of pharmaceuticals.

Review 10. C-H Functionalisation for Hydrogen Isotope Exchange.

1. Chemoselective Alpha-Deuteration of Amides via Retro-ene Reaction.