One‐pot synthesis of [2+2]‐helicate‐like macrocycle and 2+4‐μ4‐oxo tetranuclear open frame complexes : Chiroptical properties and asymmetric oxidative coupling of 2‐naphthols
Chinnaraja, E., Arunachalam, R., Pillai, R. S., Peuronen, A., Rissanen, K., & Subramanian, P. S. (2020). One‐pot synthesis of [2+2]‐helicate‐like macrocycle and 2+4‐μ4‐oxo tetranuclear open frame complexes : Chiroptical properties and asymmetric oxidative coupling of 2‐naphthols. Applied Organometallic Chemistry, 34(8), Article e5666. https://doi.org/10.1002/aoc.5666
Julkaistu sarjassa
Applied Organometallic ChemistryTekijät
Päivämäärä
2020Oppiaine
Epäorgaaninen ja analyyttinen kemiaOrgaaninen kemiaNanoscience CenterInorganic and Analytical ChemistryOrganic ChemistryNanoscience CenterTekijänoikeudet
© 2020 John Wiley & Sons, Ltd.
Synthesis of binuclear Cu(II) terminally closed [2+2]‐ double‐stranded helicate‐like macrocycles 1, 1′,1″, 2, 2′, 2″ and 2+4‐μ4‐oxo tetranuclear open frame complexes 3, 3′, 3″, 4, 4′, 4″ are established. Adapting one‐pot self‐assembly technique from simple three components systems: 1,1′‐binaphthyl‐2,2′‐diamine, 4‐methyl‐2,6‐diformyl phenol and cupric salts, the helicate‐like [2+2]‐ macrocyclic complexes 1–1″, 2–2″ and 2+4‐μ4‐oxo tetranuclear complexes 3–3″, 4–4″ were obtained by appropriately altering the reaction condition such as temperature and subcomponent ratio. Density Functional Theory (DFT) calculations were carried out for understanding the structural geometries, intermediates involved in the diverse formation of [2+2] and 2+4 frameworks. The single crystal X‐ray structures obtained for 1′, 2 and 3 confirms the self‐assembly process in line with DFT. This detailed analysis tempted us to derive a plausible mechanism for this long standing challenge in the synthesis of such macrocycles using 1,1′‐binaphthyl‐2,2′‐diamine (BNDA) and aromatic aldehyde. The chiroptical properties of enantiopure complexes and their catalytic applications in asymmetric oxidative coupling of 2‐naphthol to chiral 1,1’‐Bi‐2‐naphthol (BINOL) achieved in good yield and ee were discussed.
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Julkaisija
John Wiley & SonsISSN Hae Julkaisufoorumista
0268-2605Asiasanat
Julkaisu tutkimustietojärjestelmässä
https://converis.jyu.fi/converis/portal/detail/Publication/35425301
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Näytä kaikki kuvailutiedotKokoelmat
Rahoittaja(t)
Suomen AkatemiaRahoitusohjelmat(t)
Akatemiahanke, SALisätietoja rahoituksesta
DST‐SERB Govt. of India; Academy of Finland. Grant Numbers: 277250, 315911; DST‐SERB New DelhiLisenssi
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