Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 48, Pages 17180-17184Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201908598
Keywords
dienes; Diels-Alder reactions; gold; heterocycles; isomerizations
Categories
Funding
- NSF [CHE 1800525]
- NIGMS [R01GM123342]
- NIH [S10OD012077]
- Mellichamp Academic Initiative in Sustainability
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By using biphenyl-2-ylphosphines functionalized with a remote tertiary amino group as a ligand, readily available acetylenic amides are directly converted into 2-aminofurans devoid of any electron-withdrawing and hence deactivating/stabilizing substituents. These highly electron-rich furans have rarely been prepared, let alone applied in synthesis, because of their high reactivities and low stabilities associated with the electron-rich nature of the furan ring. In this work, these reactive furans smoothly undergo either in situ intermolecular Diels-Alder reactions to deliver highly functionalized/substituted aniline products or intramolecular ones to furnish carbazole-4-carboxylates in mostly good to excellent yields. This work offers general and expedient access to this class of little studies electron-rich furans and should lead to exciting opportunities for their applications.
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