Photocatalytic α‐Tertiary Amine Synthesis via C−H Alkylation of Unmasked Primary Amines †
Abstract: A practical, catalytic entry to α,α,α‐trisubstituted (α‐tertiary) primary amines by C−H functionalisation has long been recognised as a critical gap in the synthetic toolbox. We report a simple and scalable solution to this problem that does not require any in situ protection of the amino group and proceeds with 100 % atom‐economy. Our strategy, which uses an organic photocatalyst in combination with azide ion as a hydrogen atom transfer (HAT) catalyst, provides a direct synthesis of α‐tertiary amines, or their corresponding γ‐lactams. We anticipate that this methodology will inspire new retrosynthetic disconnections for substituted amine derivatives in organic synthesis, and particularly for challenging α‐tertiary primary amines.
- Location
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Deutsche Nationalbibliothek Frankfurt am Main
- Extent
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Online-Ressource
- Language
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Englisch
- Bibliographic citation
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Photocatalytic α‐Tertiary Amine Synthesis via C−H Alkylation of Unmasked Primary Amines † ; volume:132 ; number:35 ; year:2020 ; pages:15096-15101 ; extent:6
Angewandte Chemie ; 132, Heft 35 (2020), 15096-15101 (gesamt 6)
- Creator
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Ryder, Alison S. H.
Cunningham, William B.
Ballantyne, George
Mules, Tom
Kinsella, Anna G.
Turner‐Dore, Jacob
Alder, Catherine M.
Edwards, Lee J.
McKay, Blandine S. J.
Grayson, Matthew N.
Cresswell, Alexander J.
- DOI
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10.1002/ange.202005294
- URN
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urn:nbn:de:101:1-2022053109592532910637
- Rights
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Last update
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15.08.2025, 7:32 AM CEST
Data provider
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Associated
- Ryder, Alison S. H.
- Cunningham, William B.
- Ballantyne, George
- Mules, Tom
- Kinsella, Anna G.
- Turner‐Dore, Jacob
- Alder, Catherine M.
- Edwards, Lee J.
- McKay, Blandine S. J.
- Grayson, Matthew N.
- Cresswell, Alexander J.
Other Objects (12)
Photocatalytic α‐Tertiary Amine Synthesis via C−H Alkylation of Unmasked Primary Amines †
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Chromium‐Catalyzed Alkylation of Amines by Alcohols
Chromium‐Catalyzed Alkylation of Amines by Alcohols
N-Alkylation of functionalized amines with alcohols using a copper–gold mixed photocatalytic system
Boron-Catalyzed N-Alkylation of Amines Using Carboxylic Acids
Ruthenium-Catalyzed Alkylation of Amines and Sulfonamides with Alcohols
Stereoselective Synthesis of Tertiary Allylic Amines by Titanium‐Catalyzed Hydroaminoalkylation of Alkynes with Tertiary Amines
Author Correction: N-Alkylation of functionalized amines with alcohols using a copper–gold mixed photocatalytic system
Rhodium-catalyzed direct alkylation of benzylic amines using alkyl bromides
Ruthenium Catalyzed N ‐Alkylation of Cyclic Amines with Primary Alcohols
One-potN-alkylation of primary amines to secondary amines by gold clusters supported on porous coordination polymers
Photocatalytic α‐Tertiary Amine Synthesis via C−H Alkylation of Unmasked Primary Amines †
Chromium-Catalyzed Alkylation of Amines by Alcohols
Chromium‐Catalyzed Alkylation of Amines by Alcohols
Chromium‐Catalyzed Alkylation of Amines by Alcohols
N-Alkylation of functionalized amines with alcohols using a copper–gold mixed photocatalytic system
Boron-Catalyzed N-Alkylation of Amines Using Carboxylic Acids
Ruthenium-Catalyzed Alkylation of Amines and Sulfonamides with Alcohols
Stereoselective Synthesis of Tertiary Allylic Amines by Titanium‐Catalyzed Hydroaminoalkylation of Alkynes with Tertiary Amines
Author Correction: N-Alkylation of functionalized amines with alcohols using a copper–gold mixed photocatalytic system
Rhodium-catalyzed direct alkylation of benzylic amines using alkyl bromides
Ruthenium Catalyzed N ‐Alkylation of Cyclic Amines with Primary Alcohols
One-potN-alkylation of primary amines to secondary amines by gold clusters supported on porous coordination polymers
Photocatalytic α‐Tertiary Amine Synthesis via C−H Alkylation of Unmasked Primary Amines †
Chromium-Catalyzed Alkylation of Amines by Alcohols
Chromium‐Catalyzed Alkylation of Amines by Alcohols
Chromium‐Catalyzed Alkylation of Amines by Alcohols
N-Alkylation of functionalized amines with alcohols using a copper–gold mixed photocatalytic system
Boron-Catalyzed N-Alkylation of Amines Using Carboxylic Acids
Ruthenium-Catalyzed Alkylation of Amines and Sulfonamides with Alcohols
Stereoselective Synthesis of Tertiary Allylic Amines by Titanium‐Catalyzed Hydroaminoalkylation of Alkynes with Tertiary Amines
Author Correction: N-Alkylation of functionalized amines with alcohols using a copper–gold mixed photocatalytic system
Rhodium-catalyzed direct alkylation of benzylic amines using alkyl bromides
Ruthenium Catalyzed N ‐Alkylation of Cyclic Amines with Primary Alcohols