- Synthesis of New Axially Chiral Iodoarenes
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A new family of axially chiral iodoarenes derived from commercially available (R)-1,1′-binaphthyl-2,2′-diamine have been synthesized and employed as catalysts in Kita's enantioselective oxidative spirolactonization of propanoic acid tethered 1-naphthol. Through this study, we explored the relationship between the hypervalent iodoarene geometry and enantioselectivity, contributing to the current understanding of axial-to-central chirality transfer in organoiodine(III) catalysis.
- Bekkaye, Mathieu,Masson, Géraldine
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- Axially Chiral Bis-Cycloplatinated Binaphthalenes and Octahydro-Binaphthalenes for Efficient Circularly Polarized Phosphorescence in Solution-Processed Organic Light-Emitting Diodes
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A new series of axially chiral binuclear Pt(II) complexes with bridging ligands of binaphthalenes and octahydro-binaphthalenes and auxiliary ligands of β-diketones were designed and prepared. These complexes, identified by spectral and electrochemical met
- Wang, Lei,Xiao, Hui,Qu, Lang,Song, Jintong,Zhou, Weilan,Zhou, Xiangge,Xiang, Haifeng,Xu, Zong-Xiang
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supporting information
p. 13557 - 13566
(2021/09/11)
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- Hexafluoroisopropanol-Enabled Copper-Catalyzed Asymmetric Halogenation of Cyclic Diaryliodoniums for the Synthesis of Axially Chiral 2,2′-Dihalobiaryls
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An efficient asymmetric halogenation of cyclic diaryliodonium salts is demonstrated, which gives access to a wide range of axially chiral 2,2′-dihalobiaryls in good to excellent yields and with excellent enantioselectivities. The use of CuX with chiral bisoxazoline ligand and tetrabutylammonium halides in the unique solvent of hexafluoroisopropanol (HFIP) led to the best results in the process. The axially chiral 2,2′-dihalobiaryls can be transformed into a number of enantiopure chiral ligands that could be potentially useful in asymmetric catalysis.
- Ke, Jie,Zu, Bing,Guo, Yonghong,Li, Yingzi,He, Chuan
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supporting information
p. 329 - 333
(2021/01/13)
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- Chiral binaphthalenes bearing two pyridine ligands attached via acetylene spacers. Synthesis and coordination study
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An effective methodology has been developed for the synthesis of enantiopure 2,2′-dialkynylated 1,1′-binaphthalene derivatives. Enantiopure 2,2′-diiodo-1,1′-binaphthalene (10) provided 2,2′-diethynyl-1,1′-binaphthalene (16) in the Negishi alkynylation sup
- Kasak, Peter,Brath, Henrich,Krascsenicsova-Polakova, Katarina,Kickova, Anna,Moldovan, Natalia,Putala, Martin
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p. 1139 - 1157
(2008/09/19)
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- Elaboration of a novel effective approach to enantiopure functionalised 2,2′-dialkyl-1,1′-binaphthyls by stereoconservative cross-couplings at positions 2 and 2′
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The yield and the stereochemical outcome of methylations of 1,1 ′-binaphthyl-2,2′-dielectrophiles (ditriflate and diiodide) clearly depend on the reactivity of the organometallics used. It was found that only the Negishi reaction of
- Kasák, Peter,Putala, Martin
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p. 5279 - 5282
(2007/10/03)
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- Synthesis of Optically Active 2,2'-Dihalo-1,1'-binaphthyls via Stable Diazonium Salts
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Optically pure 2,2'-dibromo-1,1'-binaphthyl (DBBN) (5) and optically pure 2,2'-diiodo-1,1'-binaphthyl (DIBN) (6) are synthesized in preparative quantities starting from 2-naphthol.These compounds are useful for the preparation of chiral, bidentate ligands based on the 1,1'-binaphthyl system.The synthesis proceeds through a common optically active precursor, 2,2'-diamino-1,1'-binaphthyl ((R)-(+)-DABN) (2), and involves the preparation and subsequent decomposition of stable diazonium metal complexes (3 and 4).The effects of several variables, including the nature of the metal M, on these reactions is discussed, and comparison to related procedures reported in the literature is made.
- Brown, Kenneth J.,Berry, Matthew S.,Murdoch, Joseph R.
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p. 4345 - 4349
(2007/10/02)
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