New chiral 2,2′:6′,2″-terpyridine ligands from the chiral pool: synthesis, crystal structure of a rhodium complex and uses in copper- and rhodium-catalyzed enantioselective cyclopropanation of styrene

Kwong, Hoi‐Lun; Wong, Wing‐Leung; Lee, Wing‐Sze; Cheng, Leung-Shi; Wong, Wing‐Tak

doi:10.1016/s0957-4166(01)00431-1

Cited by 46 publications

(13 citation statements)

References 37 publications

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“…(−)‐Pinocarvone (−)‐ 21 was obtained on a 10 g scale from (+)‐α‐pinene through photochemical oxidation (99 %) according to the Mihelich procedure 39. (+)‐Isopinocampheol (+)‐ 24 , purchased from Aldrich, was of 96 % ee and was converted into enone 26 according to the literature protocol 42a…”

Section: Methodsmentioning

confidence: 99%

Mechanistic Dichotomy in the Asymmetric Allylation of Aldehydes with Allyltrichlorosilanes Catalyzed by Chiral Pyridine N‐Oxides

Malkov

Stončius

Bell

et al. 2013

Chemistry A European J

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Detailed kinetic and computational investigation of the enantio- and diastereoselective allylation of aldehydes 1 with allyltrichlorosilanes 5, employing the pyridine N-oxides METHOX (9) and QUINOX (10) as chiral organocatalysts, indicate that the reaction can proceed through a dissociative (cationic) or associative (neutral) mechanism: METHOX apparently favors a pentacoordinate cationic transition state, while the less sterically demanding QUINOX is likely to operate via a hexacoordinate neutral complex. In both pathways, only one molecule of the catalyst is involved in the rate- and selectivity-determining step, which is supported by both experimental and computational data.

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Section: Methodsmentioning

confidence: 99%

Mechanistic Dichotomy in the Asymmetric Allylation of Aldehydes with Allyltrichlorosilanes Catalyzed by Chiral Pyridine N‐Oxides

Malkov

Stončius

Bell

et al. 2013

Chemistry A European J

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“…Complex (I) crystallizes with two molecules of C 6 H 6 per asymmetric unit. The bond distances and angles are similar to other [RhCl 3 (η 3 -L)] complexes; L = bis(oxazolinyl)pyridine (Nishiyama et al, 1991), L = bis(pyrazolyl)pyridine (Christenson et al, 1995), L = 2,6-bis(ethylidyneimino)pyridine (Haarman et al, 1997), L = 2,3,6-tris(2-pyridyl)-1,3,5-triazine (Paul et al, 1998), L = 2,2′:6′,2′′-terpyridine (Ziegler et al, 1999;Kwong et al, 2001). and Cl2 is planar, with an average deviation of 0.042 Å; only atoms C1 and C2 of the pyrrole fragment are out of plane, by −0.100 (2) and 0.088 (2) Å, respectively.…”

Section: Data Collectionmentioning

confidence: 99%

[2,6-Bis(3,4-dihydro-2H-pyrrol-5-yl)pyridine]trichlororhodium(III) dibenzene solvate

et al. 2002

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“…To our best knowledge some terpyridine metal complexes have been employed for catalytic purposes, but 4’‐phthalonitile substituted‐terpyridines and their Pc derivatives have not been examined before. These results prompted us to investigate complexes of the terpyridine family as new class of bleach catalysts with hydrogen peroxide for laundry cleaning applications.…”

Section: Introductionmentioning

confidence: 99%

Functional Substituted Phthalocyanines Bearing Ter–pyridine Complexes as Macromolecular Oxidation Catalysts for Bleaching Systems

et al. 2017

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The present study dealing with the oxidation catalysts using in laundry bleaching process comprises of the complexion of 4’‐(N‐2‐phthalonitrile‐N‐methylamino)‐2,2’:6’,2’’‐terpyridine (2) with the related MnCl2.4H2O and CoCl2.6H2O salts in ethanol to obtain 4’‐(N‐2‐phthalonitrile‐N‐methylamino)‐2,2’:6’,2’’‐terpyridine‐Mn (II) complex (3) and 4’‐(N‐2‐phthalonitrile‐N‐methylamino)‐2,2’:6’,2’’‐terpyridine‐Co (II) complex (4). Terpyridine metal complexes substituted Zinc phthalocyanines, Tetrakis [4’‐(N‐2‐phthalonitrile‐N‐methylamino)‐2, 2’: 6’, 2’’‐terpyridine‐Mn(II) complex] phthalocyaninato zinc(II) (5) and Tetrakis [4’‐(N‐2‐phthalonitrile‐N‐methylamino)‐2,2’:6’,2’’‐terpyridine‐Co(II) complex] phthalocyaninato zinc(II) (6) were also prepared by the tetramerization of the terpyridine‐metal complexes (3, 4) in the presence of ZnCl2. FT‐IR, 1H‐NMR, 13C‐NMR, UV‐Vis, ESI‐MS and MALDI‐MS spectra were applied to characterize the prepared compounds. 4‐nitrophthalonitrile and some other starting materials crystallized in the synthetic pathway. 4‐nitrophthalonitrile crystalizes in different morphology and 4’‐(N‐2‐ Hydroxyehyl‐N‐methylamino)‐2, 2’ : 6’, 2’’‐ terpyridine (1) crystallizes in the monoclinic, space group. The compound 2 and 3 crystallize in the monoclinic space group. The bleach performances of the prepared terpyridine complexes (3, 4) and their phthalocyanine derivatives (5, 6) were examined by the degradation of Morin dye by using online spectrophotometric method (OSM).

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New chiral 2,2′:6′,2″-terpyridine ligands from the chiral pool: synthesis, crystal structure of a rhodium complex and uses in copper- and rhodium-catalyzed enantioselective cyclopropanation of styrene

Cited by 46 publications

References 37 publications

Mechanistic Dichotomy in the Asymmetric Allylation of Aldehydes with Allyltrichlorosilanes Catalyzed by Chiral Pyridine N‐Oxides

Mechanistic Dichotomy in the Asymmetric Allylation of Aldehydes with Allyltrichlorosilanes Catalyzed by Chiral Pyridine N‐Oxides

[2,6-Bis(3,4-dihydro-2H-pyrrol-5-yl)pyridine]trichlororhodium(III) dibenzene solvate

Functional Substituted Phthalocyanines Bearing Ter–pyridine Complexes as Macromolecular Oxidation Catalysts for Bleaching Systems

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