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

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(C(2)H(4))(2)](2) and BINAP was determined to be the most effective catalyst to promote the 1,4-conjugate addition reactions of...

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Autores principales: Guo, Fenghai, McGilvary, Matthew A., Jeffries, Malcolm C., Graves, Briana N., Graham, Shekinah A., Wu, Yuelin
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2017
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6154701/
https://www.ncbi.nlm.nih.gov/pubmed/28468302
http://dx.doi.org/10.3390/molecules22050723
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author Guo, Fenghai
McGilvary, Matthew A.
Jeffries, Malcolm C.
Graves, Briana N.
Graham, Shekinah A.
Wu, Yuelin
author_facet Guo, Fenghai
McGilvary, Matthew A.
Jeffries, Malcolm C.
Graves, Briana N.
Graham, Shekinah A.
Wu, Yuelin
author_sort Guo, Fenghai
collection PubMed
description 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(C(2)H(4))(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.
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spelling pubmed-61547012018-11-13 Rhodium(I)-Complexes Catalyzed 1,4-Conjugate Addition of Arylzinc Chlorides to N-Boc-4-pyridone Guo, Fenghai McGilvary, Matthew A. Jeffries, Malcolm C. Graves, Briana N. Graham, Shekinah A. Wu, Yuelin Molecules Article 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(C(2)H(4))(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. MDPI 2017-05-01 /pmc/articles/PMC6154701/ /pubmed/28468302 http://dx.doi.org/10.3390/molecules22050723 Text en © 2017 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Guo, Fenghai
McGilvary, Matthew A.
Jeffries, Malcolm C.
Graves, Briana N.
Graham, Shekinah A.
Wu, Yuelin
Rhodium(I)-Complexes Catalyzed 1,4-Conjugate Addition of Arylzinc Chlorides to N-Boc-4-pyridone
title Rhodium(I)-Complexes Catalyzed 1,4-Conjugate Addition of Arylzinc Chlorides to N-Boc-4-pyridone
title_full Rhodium(I)-Complexes Catalyzed 1,4-Conjugate Addition of Arylzinc Chlorides to N-Boc-4-pyridone
title_fullStr Rhodium(I)-Complexes Catalyzed 1,4-Conjugate Addition of Arylzinc Chlorides to N-Boc-4-pyridone
title_full_unstemmed Rhodium(I)-Complexes Catalyzed 1,4-Conjugate Addition of Arylzinc Chlorides to N-Boc-4-pyridone
title_short Rhodium(I)-Complexes Catalyzed 1,4-Conjugate Addition of Arylzinc Chlorides to N-Boc-4-pyridone
title_sort rhodium(i)-complexes catalyzed 1,4-conjugate addition of arylzinc chlorides to n-boc-4-pyridone
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6154701/
https://www.ncbi.nlm.nih.gov/pubmed/28468302
http://dx.doi.org/10.3390/molecules22050723
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