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Molecules 2017, 22(5), 723; doi:10.3390/molecules22050723

Rhodium(I)-Complexes Catalyzed 1,4-Conjugate Addition of Arylzinc Chlorides to N-Boc-4-pyridone

1
Department of Chemistry, Winston-Salem State University, Winston Salem, NC 27110, USA
2
School of Chemical and Environmental Engineering, Shanghai Institute of Technology, Shanghai 201418, China
*
Author to whom correspondence should be addressed.
Academic Editor: Wim Dehaen
Received: 15 March 2017 / Revised: 27 April 2017 / Accepted: 27 April 2017 / Published: 1 May 2017
(This article belongs to the Collection Heterocyclic Compounds)
View Full-Text   |   Download PDF [885 KB, uploaded 9 May 2017]   |  

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. View Full-Text
Keywords: N-boc-4-pyridone; rhodium (I)-complexes; conjugate addition; 2,3-dihydropyridones N-boc-4-pyridone; rhodium (I)-complexes; conjugate addition; 2,3-dihydropyridones
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Guo, F.; McGilvary, M.A.; Jeffries, M.C.; Graves, B.N.; Graham, S.A.; Wu, Y. Rhodium(I)-Complexes Catalyzed 1,4-Conjugate Addition of Arylzinc Chlorides to N-Boc-4-pyridone. Molecules 2017, 22, 723.

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