Continuous-Flow Synthesis and Derivatization of Aziridines through Palladium-Catalyzed C(sp3)−H Activation
A continuous‐flow synthesis of aziridines by palladium‐catalyzed C(sp3)−H activation is described. The new flow reaction could be combined with an aziridine‐ring‐opening reaction to give highly functionalized aliphatic amines through a consecutive process. A predictive mechanistic model was develope...
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| Published in | Angewandte Chemie (International ed.) Vol. 55; no. 31; pp. 8878 - 8883 |
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| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
| Published |
WEINHEIM
Blackwell Publishing Ltd
25.07.2016
Wiley Wiley Subscription Services, Inc John Wiley and Sons Inc |
| Edition | International ed. in English |
| Subjects | |
| Online Access | Get full text |
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| Abstract | A continuous‐flow synthesis of aziridines by palladium‐catalyzed C(sp3)−H activation is described. The new flow reaction could be combined with an aziridine‐ring‐opening reaction to give highly functionalized aliphatic amines through a consecutive process. A predictive mechanistic model was developed and used to design the C−H activation flow process and illustrates an approach towards first‐principles design based on novel catalytic reactions.
Keep up with the flow! A predictive mechanistic model was developed and used to design a flow process for C−H activation. The resulting continuous‐flow synthesis of aziridines through palladium‐catalyzed C(sp3)−H activation was combined with ring opening of the aziridine in flow to give highly functionalized aliphatic amines in a consecutive process involving the capture and release of the aziridine intermediate (see scheme). |
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| AbstractList | A continuous-flow synthesis of aziridines by palladium-catalyzed C(sp3)-H activation is described. The new flow reaction could be combined with an aziridine-ring-opening reaction to give highly functionalized aliphatic amines through a consecutive process. A predictive mechanistic model was developed and used to design the C-H activation flow process and illustrates an approach towards first-principles design based on novel catalytic reactions. A continuous‐flow synthesis of aziridines by palladium‐catalyzed C(sp 3 )−H activation is described. The new flow reaction could be combined with an aziridine‐ring‐opening reaction to give highly functionalized aliphatic amines through a consecutive process. A predictive mechanistic model was developed and used to design the C−H activation flow process and illustrates an approach towards first‐principles design based on novel catalytic reactions. Abstract A continuous‐flow synthesis of aziridines by palladium‐catalyzed C(sp 3 )−H activation is described. The new flow reaction could be combined with an aziridine‐ring‐opening reaction to give highly functionalized aliphatic amines through a consecutive process. A predictive mechanistic model was developed and used to design the C−H activation flow process and illustrates an approach towards first‐principles design based on novel catalytic reactions. A continuous-flow synthesis of aziridines by palladium-catalyzed C(sp(3) )-H activation is described. The new flow reaction could be combined with an aziridine-ring-opening reaction to give highly functionalized aliphatic amines through a consecutive process. A predictive mechanistic model was developed and used to design the C-H activation flow process and illustrates an approach towards first-principles design based on novel catalytic reactions. A continuous‐flow synthesis of aziridines by palladium‐catalyzed C(sp3)−H activation is described. The new flow reaction could be combined with an aziridine‐ring‐opening reaction to give highly functionalized aliphatic amines through a consecutive process. A predictive mechanistic model was developed and used to design the C−H activation flow process and illustrates an approach towards first‐principles design based on novel catalytic reactions. Keep up with the flow! A predictive mechanistic model was developed and used to design a flow process for C−H activation. The resulting continuous‐flow synthesis of aziridines through palladium‐catalyzed C(sp3)−H activation was combined with ring opening of the aziridine in flow to give highly functionalized aliphatic amines in a consecutive process involving the capture and release of the aziridine intermediate (see scheme). |
| Author | Kabeshov, Mikhail A. Gaunt, Matthew J. Zakrzewski, Jacek Smalley, Adam P. Lapkin, Alexei A. |
| AuthorAffiliation | 1 Department of Chemical Engineering and Biotechnology University of Cambridge Pembroke Street Cambridge CB2 3RA UK 2 Chemistry Department University of Cambridge Lensfield Rd Cambridge CB2 1EW UK |
| AuthorAffiliation_xml | – name: 2 Chemistry Department University of Cambridge Lensfield Rd Cambridge CB2 1EW UK – name: 1 Department of Chemical Engineering and Biotechnology University of Cambridge Pembroke Street Cambridge CB2 3RA UK |
| Author_xml | – sequence: 1 givenname: Jacek surname: Zakrzewski fullname: Zakrzewski, Jacek organization: Department of Chemical Engineering and Biotechnology, University of Cambridge, Pembroke Street, CB2 3RA, Cambridge, UK – sequence: 2 givenname: Adam P. surname: Smalley fullname: Smalley, Adam P. organization: Chemistry Department, University of Cambridge, Lensfield Rd, CB2 1EW, Cambridge, UK – sequence: 3 givenname: Mikhail A. surname: Kabeshov fullname: Kabeshov, Mikhail A. organization: Chemistry Department, University of Cambridge, Lensfield Rd, CB2 1EW, Cambridge, UK – sequence: 4 givenname: Matthew J. surname: Gaunt fullname: Gaunt, Matthew J. email: mjg32@cam.ac.uk organization: Chemistry Department, University of Cambridge, Lensfield Rd, CB2 1EW, Cambridge, UK – sequence: 5 givenname: Alexei A. surname: Lapkin fullname: Lapkin, Alexei A. email: aal35@cam.ac.uk organization: Department of Chemical Engineering and Biotechnology, University of Cambridge, Pembroke Street, CB2 3RA, Cambridge, UK |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/27304395$$D View this record in MEDLINE/PubMed |
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| Keywords | aziridines palladium catalysis REACTORS continuous-flow synthesis DIRECT ARYLATION MECHANISM SAFE H BOND FUNCTIONALIZATION CLAISEN REARRANGEMENT C-H activation ring opening CHEMISTRY METAL BATCH TECHNOLOGY C−H activation |
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| Snippet | A continuous‐flow synthesis of aziridines by palladium‐catalyzed C(sp3)−H activation is described. The new flow reaction could be combined with an... A continuous-flow synthesis of aziridines by palladium-catalyzed C(sp(3))-H activation is described. The new flow reaction could be combined with an... A continuous-flow synthesis of aziridines by palladium-catalyzed C(sp(3) )-H activation is described. The new flow reaction could be combined with an... Abstract A continuous‐flow synthesis of aziridines by palladium‐catalyzed C(sp 3 )−H activation is described. The new flow reaction could be combined with an... A continuous-flow synthesis of aziridines by palladium-catalyzed C(sp3)-H activation is described. The new flow reaction could be combined with an... A continuous‐flow synthesis of aziridines by palladium‐catalyzed C(sp 3 )−H activation is described. The new flow reaction could be combined with an... |
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| SubjectTerms | aziridines Chemistry Chemistry, Multidisciplinary Communication Communications continuous-flow synthesis C−H activation palladium catalysis Physical Sciences ring opening Science & Technology |
| Title | Continuous-Flow Synthesis and Derivatization of Aziridines through Palladium-Catalyzed C(sp3)−H Activation |
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