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Literature DB >> 19388020

Multistep synthesis using modular flow reactors: Bestmann-Ohira reagent for the formation of alkynes and triazoles.

Ian R Baxendale¹, Steven V Ley, Andrew C Mansfield, Christopher D Smith.

Abstract

Multistep in flow: The Seyferth-Gilbert reagent 1 has been applied in a flow system to rapidly synthesize terminal alkynes. The system has been further applied to synthesize triazole 3 from alcohol 2 in a three-step oxidation/homologation/copper(I)-catalyzed azide-alkyne cycloaddition sequence without isolation of intermediates (see scheme).

Entities: Chemical

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Year: 2009 PMID： 19388020 DOI： 10.1002/anie.200900970

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

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Cited

15 in total

1. The flow synthesis of heterocycles for natural product and medicinal chemistry applications.

Authors: Marcus Baumann; Ian R Baxendale; Steven V Ley
Journal: Mol Divers Date: 2010-10-20 Impact factor: 2.943

Review 2. The past, present and potential for microfluidic reactor technology in chemical synthesis.

Authors: Katherine S Elvira; Xavier Casadevall i Solvas; Robert C R Wootton; Andrew J deMello
Journal: Nat Chem Date: 2013-10-13 Impact factor: 24.427

3. Organic synthesis: Scavengers in full flow.

Authors: Peter H Seeberger
Journal: Nat Chem Date: 2009-07 Impact factor: 24.427

4. In-Line Purification: A Key Component to Facilitate Drug Synthesis and Process Development in Medicinal Chemistry.

Authors: Nopphon Weeranoppanant; Andrea Adamo
Journal: ACS Med Chem Lett Date: 2019-12-12 Impact factor: 4.345

5. In situ generation and intramolecular Schmidt reaction of keto azides in a microwave-assisted flow format.

Authors: Thomas O Painter; Paul D Thornton; Mario Orestano; Conrad Santini; Michael G Organ; Jeffrey Aubé
Journal: Chemistry Date: 2011-07-27 Impact factor: 5.236

6. One-step continuous flow synthesis of highly substituted pyrrole-3-carboxylic acid derivatives via in situ hydrolysis of tert-butyl esters.

Authors: Ananda Herath; Nicholas D P Cosford
Journal: Org Lett Date: 2010-10-21 Impact factor: 6.005

Multistep synthesis using modular flow reactors: Bestmann-Ohira reagent for the formation of alkynes and triazoles.

1. The flow synthesis of heterocycles for natural product and medicinal chemistry applications.

Review 2. The past, present and potential for microfluidic reactor technology in chemical synthesis.

3. Organic synthesis: Scavengers in full flow.

4. In-Line Purification: A Key Component to Facilitate Drug Synthesis and Process Development in Medicinal Chemistry.

5. In situ generation and intramolecular Schmidt reaction of keto azides in a microwave-assisted flow format.

6. One-step continuous flow synthesis of highly substituted pyrrole-3-carboxylic acid derivatives via in situ hydrolysis of tert-butyl esters.

7. Fully automated continuous flow synthesis of highly functionalized imidazo[1,2-a] heterocycles.

8. Continuous proline catalysis via leaching of solid proline.

9. Zinc mediated azide-alkyne ligation to 1,5- and 1,4,5-substituted 1,2,3-triazoles.

10. Flow photochemistry: Old light through new windows.