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- Title
Rhodium(I)-Complexes Catalyzed 1,4-Conjugate Addition of Arylzinc Chlorides to N-Boc-4-pyridone.
- Authors
Fenghai Guo; McGilvary, Matthew A.; Jeffries, Malcolm C.; Graves, Briana N.; Graham, Shekinah A.; Yuelin Wu
- Abstract
Rhodium(I)-complexes catalyzed the 1,4-conjugate addition of arylzinc chlorides to N-Boc-4-pyridone in the presence of chlorotrimethylsilane (TMSCl). A combination of [RhCl(C2H4)2]2 and BINAP was determined to be the most effective catalyst to promote the 1,4-conjugate addition reactions of arylzinc chlorides to N-Boc-4-pyridone. A broad scope of arylzinc reagents with both electron-withdrawing and electron-donating substituents on the aromatic ring successfully underwent 1,4-conjugate addition to N-Boc-4-pyridone to afford versatile 1,4-adducts 2-substituted-2,3-dihydropyridones in good to excellent yields (up to 91%) and excellent ee (up to 96%) when (S)-BINAP was used as chiral ligand.
- Subjects
RHODIUM compounds; ARYL group; PYRIDONE derivatives; ELECTRON donor-acceptor complexes; CHEMICAL reagents; LIGANDS (Biochemistry)
- Publication
Molecules, 2017, Vol 22, Issue 5, p723
- ISSN
1420-3049
- Publication type
Article
- DOI
10.3390/molecules22050723