Journal
SYNOPEN
Volume 4, Issue 4, Pages 123-131Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0040-1706004
Keywords
C-H bond functionalization; redox-neutral; redox-annulation; denitration; decarboxylative annulation
Categories
Funding
- NIH-NIGMS [R01GM101389]
- National Science Foundation [1828064]
- University of Florida
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1828064] Funding Source: National Science Foundation
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Amines such as 1,2,3,4-tetrahydroisoquinoline undergo redox--neutral annulations with ortho-(nitromethyl)benzaldehyde. Benzoic- acid acts as a promoter in these reactions, which involve concurrent amine alpha-C-H bond and N-H bond functionalization. Subsequent removal of the nitro group provides access to tetrahydroprotoberberines not accessible via typical redox-annulations. Also reported are decarboxylative annulations of ortho-(nitromethyl)benzaldehyde with proline and pipecolic acid.
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