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  Automated radial synthesis of organic molecules

Chatterjee, S., Guidi, M., Seeberger, P. H., & Gilmore, K. (2020). Automated radial synthesis of organic molecules. Nature, 579(7799), 379-384. doi:10.1038/s41586-020-2083-5.

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Item Permalink: http://hdl.handle.net/21.11116/0000-0005-EBC7-2 Version Permalink: http://hdl.handle.net/21.11116/0000-0006-569D-9
Genre: Journal Article

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 Creators:
Chatterjee, Sourav1, Author              
Guidi, Mara1, Author              
Seeberger, Peter H.2, Author              
Gilmore, Kerry1, Author              
Affiliations:
1Kerry Gilmore, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society, ou_1863304              
2Peter H. Seeberger - Automated Systems, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society, ou_1863306              

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Free keywords: Automation; Flow chemistry; Synthetic chemistry, methodology
 Abstract: Automated synthesis platforms accelerate and simplify the preparation of molecules by removing the physical barriers to organic synthesis. This provides unrestricted access to biopolymers and small molecules via reproducible and directly comparable chemical processes. Current automated multistep syntheses rely on either iterative or linear processes, and require compromises in terms of versatility and the use of equipment. Here we report an approach towards the automated synthesis of small molecules, based on a series of continuous flow modules that are radially arranged around a central switching station. Using this approach, concise volumes can be exposed to any reaction conditions required for a desired transformation. Sequential, non-simultaneous reactions can be combined to perform multistep processes, enabling the use of variable flow rates, reuse of reactors under different conditions, and the storage of intermediates. This fully automated instrument is capable of both linear and convergent syntheses and does not require manual reconfiguration between different processes. The capabilities of this approach are demonstrated by performing optimizations and multistep syntheses of targets, varying concentrations via inline dilutions, exploring several strategies for the multistep synthesis of the anticonvulsant drug rufinamide, synthesizing eighteen compounds of two derivative libraries that are prepared using different reaction pathways and chemistries, and using the same reagents to perform metallaphotoredox carbon–nitrogen cross-couplings in a photochemical module—all without instrument reconfiguration.

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Language(s): eng - English
 Dates: 2020-03-182020
 Publication Status: Published in print
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 Rev. Method: -
 Identifiers: DOI: 10.1038/s41586-020-2083-5
Other: MS erbeten. AP23032020
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Title: Nature
  Abbreviation : Nature
Source Genre: Journal
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Publ. Info: London : Nature Publishing Group
Pages: - Volume / Issue: 579 (7799) Sequence Number: - Start / End Page: 379 - 384 Identifier: ISSN: 0028-0836