2,2‘,5,5‘-Tetramethyl-4,4‘-bis(diphenylphoshino)-3,3‘-bithiophene: A New, Very Efficient, Easily Accessible, Chiral Biheteroaromatic Ligand for Homogeneous Stereoselective Catalysis
1
Dipartimento di Chimica Organica e Industriale dell'Università, via Golgi 19-20133-Milano, Italy, Dipartimento di Scienze Chimiche, Fisiche e Matematiche dell'Università dell'Insubria, via Lucini 3-22100-Como, Italy, Dipartimento di Chimica Inorganica, Metallorganica e Analitica dell'Università, via Golgi 19-20133-Milano, Italy, and Chemi S.p.A., via dei Lavoratori 54-20092-Cinisello Balsamo, Italy
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Publication type: Journal Article
Publication date: 2000-03-09
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
10774024
Organic Chemistry
Abstract
The four-step straightforward synthesis of enantiopure (+)- and (-)-2,2',5,5'-tetramethyl-4,4'-bis-(diphenylphoshino)-3,3'-bithiophene (tetraMe-BITIOP), a new C2-symmetry chelating ligand for transition metals, is described, starting from 2,5-dimethylthiophene. The complexes of this electron-rich diphosphine with Ru(II) and Rh(I) were used as catalysts in some homogeneous hydrogenation reactions of prostereogenic carbonyl functions of alpha- and beta-ketoesters, of prostereogenic carbon-carbon double bonds of substituted acrylic acids, and of N-acetylenamino acids. The enantiomeric excesses were found to be excellent in all the experiments and comparable with the best results reported in the literature for the same reactions, carried out under similar experimental conditions, with the metal complexes of the most popular chiral diphosphine ligands as catalysts.
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127
Total citations:
127
Citations from 2024:
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(3.14%)
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Benincori T. et al. 2,2‘,5,5‘-Tetramethyl-4,4‘-bis(diphenylphoshino)-3,3‘-bithiophene: A New, Very Efficient, Easily Accessible, Chiral Biheteroaromatic Ligand for Homogeneous Stereoselective Catalysis // Journal of Organic Chemistry. 2000. Vol. 65. No. 7. pp. 2043-2047.
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Benincori T., Cesarotti E., Piccolo O., Sannicolò F. 2,2‘,5,5‘-Tetramethyl-4,4‘-bis(diphenylphoshino)-3,3‘-bithiophene: A New, Very Efficient, Easily Accessible, Chiral Biheteroaromatic Ligand for Homogeneous Stereoselective Catalysis // Journal of Organic Chemistry. 2000. Vol. 65. No. 7. pp. 2043-2047.
Cite this
RIS
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TY - JOUR
DO - 10.1021/jo991533x
UR - https://doi.org/10.1021/jo991533x
TI - 2,2‘,5,5‘-Tetramethyl-4,4‘-bis(diphenylphoshino)-3,3‘-bithiophene: A New, Very Efficient, Easily Accessible, Chiral Biheteroaromatic Ligand for Homogeneous Stereoselective Catalysis
T2 - Journal of Organic Chemistry
AU - Benincori, Tiziana
AU - Cesarotti, Edoardo
AU - Piccolo, O.
AU - Sannicolò, Franco
PY - 2000
DA - 2000/03/09
PB - American Chemical Society (ACS)
SP - 2043-2047
IS - 7
VL - 65
PMID - 10774024
SN - 0022-3263
SN - 1520-6904
ER -
Cite this
BibTex (up to 50 authors)
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@article{2000_Benincori,
author = {Tiziana Benincori and Edoardo Cesarotti and O. Piccolo and Franco Sannicolò},
title = {2,2‘,5,5‘-Tetramethyl-4,4‘-bis(diphenylphoshino)-3,3‘-bithiophene: A New, Very Efficient, Easily Accessible, Chiral Biheteroaromatic Ligand for Homogeneous Stereoselective Catalysis},
journal = {Journal of Organic Chemistry},
year = {2000},
volume = {65},
publisher = {American Chemical Society (ACS)},
month = {mar},
url = {https://doi.org/10.1021/jo991533x},
number = {7},
pages = {2043--2047},
doi = {10.1021/jo991533x}
}
Cite this
MLA
Copy
Benincori, Tiziana, et al. “2,2‘,5,5‘-Tetramethyl-4,4‘-bis(diphenylphoshino)-3,3‘-bithiophene: A New, Very Efficient, Easily Accessible, Chiral Biheteroaromatic Ligand for Homogeneous Stereoselective Catalysis.” Journal of Organic Chemistry, vol. 65, no. 7, Mar. 2000, pp. 2043-2047. https://doi.org/10.1021/jo991533x.