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.

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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
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article

Synthesis of morpholine derivatives from 1,3-dienes and N -arylaminoalcohols by palladium-catalyzed sequential C–N and C–O bond formation

Ayumi Yamaguchi, Nobuki Katayama, Tetsuaki Fujihara, Yasushi Obora et al.
Organic & Biomolecular Chemistry
Catalytic C–H Functionalization Methods
article

Synthesis of morpholine derivatives from 1,3-dienes and N -arylaminoalcohols by palladium-catalyzed sequential C–N and C–O bond formation

Ayumi Yamaguchi, Nobuki Katayama, Tetsuaki Fujihara, Yasushi Obora, Kazuki Tabaru
article en

Abstract

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.

Organic & Biomolecular ChemistryVol. 24(3)
Kyoto University (JP), Kansai University (JP)
Openalex Percentile: Top 69%
Catalytic C–H Functionalization Methods
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