Novel π-expanded chrysene-based axially chiral molecules: 1,1′-bichrysene-2,2′-diols and thiophene analogs

An, Shujie; Guo-feng, Tang; Zhong, Yaling; Ma, Li; Liu, Qiancai

doi:10.1177/1747519820914837

Cited by 1 publication

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References 17 publications

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“…It was used for asymmetric synthesis. Transition metal-catalyzed synthesis of compounds 3 from 1 were also developed. − The 6,6′-di(boronic acid or ester)-substituted BINOLs 4 were synthesized as the precursors to prepare other derivatives of BINOL via the Suzuki coupling reactions. − Compounds 5 with various alkyl, aryl, vinyl, and alkynyl substituents at the 6,6′-positions were prepared for a variety of study. − The fluorous BINOL ligands such as the 6,6′-di(perfluoroalkylsilyl)BINOL ( R )- 6 was synthesized for the biphasic (organic/fluorous) asymmetric catalysis. , Other 6,6′-disilylBINOLs were also prepared for asymmetric catalysis …”

Section: Electrophilic Substitution At 6-positionmentioning

confidence: 99%

Regioselective Substitution of BINOL

2024

Chem. Rev.

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1,1′-Bi-2-naphthol (BINOL) has been extensively used as the chirality source in the fields of molecular recognition, asymmetric synthesis, and materials science. The direct electrophilic substitution at the aromatic rings of the optically active BINOL has been developed as one of the most convenient strategies to structurally modify BINOL for diverse applications. High regioselectivity has been achieved for the reaction of BINOL with electrophiles. Depending upon the reaction conditions and substitution patterns, various functional groups can be introduced to the specific positions, such as the 6-, 5-, 4-, and 3-positions, of BINOL. Ortho-lithiation at the 3-position directed by the functional groups at the 2-position of BINOL have been extensively used to prepare the 3- and 3,3′-substituted BINOLs. The use of transition metal-catalyzed C–H activation has also been explored to functionalize BINOL at the 3-, 4-, 5-, 6-, and 7-positions. These regioselective substitutions of BINOL have allowed the construction of tremendous amount of BINOL derivatives with fascinating structures and properties as reviewed in this article. Examples for the applications of the optically active BINOLs with varying substitutions in asymmetric catalysis, molecular recognition, chiral sensing and materials are also provided.

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Section: Electrophilic Substitution At 6-positionmentioning

confidence: 99%

Regioselective Substitution of BINOL

2024

Chem. Rev.

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Novel π-expanded chrysene-based axially chiral molecules: 1,1′-bichrysene-2,2′-diols and thiophene analogs

Cited by 1 publication

References 17 publications

Regioselective Substitution of BINOL

Regioselective Substitution of BINOL

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