Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 35, Pages 14986-14991Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202005294
Keywords
amines; C-H activation; photocatalysis; radicals; spiro compounds
Categories
Funding
- Engineering and Physical Sciences Research Council [EP/L016354/1]
- Royal Society [UF150533]
- University of Bath
- Centre for Sustainable Chemical Technologies (CSCT)
- EPSRC
- AstraZeneca
- Dial-a-Molecule network
- EPSRC [EP/S028595/1, EP/P007589/1] Funding Source: UKRI
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A practical, catalytic entry to alpha,alpha,alpha-trisubstituted (alpha-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 alpha-tertiary amines, or their corresponding gamma-lactams. We anticipate that this methodology will inspire new retrosynthetic disconnections for substituted amine derivatives in organic synthesis, and particularly for challenging alpha-tertiary primary amines.
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