Monohydride-Dichloro Rhodium(III) Complexes with Chiral Diphosphine Ligands as Catalysts for Asymmetric Hydrogenation of Olefinic Substrates.
asymmetric hydrogenation
monohydride
mononuclear complexes
rhodium
simple olefins
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
17 Jul 2020
17 Jul 2020
Historique:
received:
01
02
2020
pubmed:
13
3
2020
medline:
13
3
2020
entrez:
13
3
2020
Statut:
ppublish
Résumé
We report full details of the synthesis and characterization of monohydride-dichloro rhodium(III) complexes bearing chiral diphosphine ligands, such as (S)-BINAP, (S)-DM-SEGPHOS, and (S)-DTBM-SEGPHOS, producing cationic triply chloride bridged dinuclear rhodium(III) complexes (1 a: (S)-BINAP; 1 b: (S)-DM-SEGPHOS) and a neutral mononuclear monohydride-dichloro rhodium(III) complex (1 c: (S)-DTBM-SEGPHOS) in high yield and high purity. Their solid state structure and solution behavior were determined by crystallographic studies as well as full spectral data, including DOSY NMR spectroscopy. Among these three complexes, 1 c has a rigid pocket surrounded by two chloride atoms bound to the rhodium atom together with one tBu group of (S)-DTBM-SEGPHOS for fitting to simple olefins without any coordinating functional groups. Complex 1 c exhibited superior catalytic activity and enantioselectivity for asymmetric hydrogenation of exo-olefins and olefinic substrates. The catalytic activity of 1 c was compared with that of well-demonstrated dihydride species derived in situ from rhodium(I) precursors such as [Rh(cod)Cl]
Identifiants
pubmed: 32163213
doi: 10.1002/chem.202000542
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
8749-8759Subventions
Organisme : Japan Society for the Promotion of Science
ID : JP15H05808
Organisme : Japan Society for the Promotion of Science
ID : JP15K21707
Informations de copyright
© 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
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An acetyl group of (+)-1-(2-phenylindolin-1-yl)ethan-1-one ((R)-11 a) (>99 % ee, 23.6 mg, 0.10 mmol) was deprotected with few drops of conc. H2SO4 in EtOH (2.0 mL)/H2O (1.0 mL) under reflux conditions for 12 h to afford (+)-R-2-phenyl indoline (>99 % ee, 16.0 mg, 0.082 mmol) in 82 % yield. (+)-R-2-phenyl indoline, yellow solid; 1H NMR (CDCl3, 400 MHz, 30 °C): δ=7.42 (d, J=7.3 Hz, 2 H), 7.34 (appt, J=7.4, 2 H), 7.28 (d, J=7.2 Hz, 1 H), 7.12-7.03 (m, 2 H), 6.74 (t, J=7.4 Hz, 1 H), 6.68 (d, J=7.8 Hz, 1 H), 4.96 (t, J=8.9 Hz, 1 H), 3.45 (dd, J=15.9 Hz, J=9.0 Hz, 1 H), 3.45 ppm (dd, J=15.9 Hz, J=8.8 Hz, 1 H); 13C{1H} NMR (CDCl3, 100 MHz, 30 °C): δ=151.0, 144.7, 128.8, 128.3, 127.7, 127.6, 126.4, 124.7, 119.1, 109.1, 63.7, 39.7 ppm; HPLC (Daicel OD-H, temperature: 30 °C, hexane/iPrOH=80:20, detector: 215 nm, flow rate: 1.0 mL min−1, t1(−)=9.6 min, t2(+)=15.0 min); [α]20D =+89.4 (c=0.33 in CHCl3, >99 % ee). Absolute configuration was determined by using literature data. K. Saito, Y. Shibata, M. Yamanaka, T. Akiyama, J. Am. Chem. Soc. 2013, 135, 11740-11743.
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