Synthesis of morpholine derivatives from 1,3-dienes and <i>N</i> -arylaminoalcohols by palladium-catalyzed sequential C–N and C–O bond formation
We developed a palladium-catalyzed oxidative coupling of 1,3-dienes with <i>N</i>-arylaminoalcohols to synthesize morpholine derivatives. Using a copper salt and 1,4-benzoquinone with molecular oxygen afforded high yields. DFT calculations elucidated the chemical selectivity and revealed that 1,4-benzoquinone acts as a ligand promoting reductive elimination, offering mechanistic insight into the catalytic cycle.
Authors
- Ayumi Yamaguchi
- Nobuki Katayama (ORCID: https://orcid.org/0000-0003-4649-3747)
- Tetsuaki Fujihara (ORCID: https://orcid.org/0000-0002-6687-2528)
- Yasushi Obora (ORCID: https://orcid.org/0000-0003-3702-9969)
- Kazuki Tabaru (ORCID: https://orcid.org/0000-0001-5587-5670)
Institutions
- Kyoto University (JP)
- Kansai University (JP)
Publication Details
- Journal
- Organic & Biomolecular Chemistry
- Published
- 2025-12-17
- DOI
- https://doi.org/10.1039/d5ob01744k
- Primary Topic
- Catalytic C–H Functionalization Methods
- Type
- article
- Field-Weighted Citation Impact
- 0.00