Oxidation of BINOLs by Hypervalent Iodine Reagents: Facile Synthesis of Xanthenes and Lactones

Zhang, Huaiyuan; Wirth, Thomas

doi:10.1002/chem.202200181

Cited by 9 publications

(4 citation statements)

References 81 publications

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“…These compounds were used in combination with BH 3 ·THF to promote the asymmetric Diels–Alder reactions. ( R )- or ( S )- 133 were also used to prepare other BINOL-based compounds for various applications. − …”

Section: Ortho-lithiation At 3-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: Ortho-lithiation At 3-positionmentioning

confidence: 99%

Regioselective Substitution of BINOL

2024

Chem. Rev.

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“…Additionally, various substituted groups on five-membered cyclic aryliodoniums (121l−n), including alkyl and halogen, are suitable for this transformation and deliver functionalized 1,2,3-triazole derivatives (123l−n) successfully. Furthermore, it is worth mentioning that these axially chiral triazole-containing scaffolds could serve as powerful substrates for the construction of different chiral phosphine ligands (124,125).…”

Section: Construction Of Biaryl Atropisomers Via Single N-arylationmentioning

confidence: 99%

“…Chiral hypervalent iodine chemistry has been steadily increasing interest in recent years, especially the acyclic aryliodoniums as potential chiral reagents in asymmetric synthesis over the last decades . Among them, binaphthyl-based chiral iodoniums 36 have interesting properties as a result of the naphthyl moieties restricting the axial rotation (Scheme A). − Several approaches to binaphthyl-based chiral acyclic aryliodoniums are disclosed in the past years. Recently, Wirth et al have prepared novel binaphthyl-based chiral acyclic iodonium reagents 40 from λ 3 -iodanes and BINOL ( R )-analogues 38 , as depicted in Scheme B.…”

Section: Advance In Design and Synthesis Of Cyclic Aryliodoniumsmentioning

confidence: 99%

Recent Progress in Cyclic Aryliodonium Chemistry: Syntheses and Applications

et al. 2023

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Hypervalent aryliodoumiums are intensively investigated as arylating agents. They are excellent surrogates to aryl halides, and moreover they exhibit better reactivity, which allows the corresponding arylation reactions to be performed under mild conditions. In the past decades, acyclic aryliodoniums are widely explored as arylation agents. However, the unmet need for acyclic aryliodoniums is the improvement of their notoriously low reaction economy because the coproduced aryl iodides during the arylation are often wasted. Cyclic aryliodoniums have their intrinsic advantage in terms of reaction economy, and they have started to receive considerable attention due to their valuable synthetic applications to initiate cascade reactions, which can enable the construction of complex structures, including polycycles with potential pharmaceutical and functional properties. Here, we are summarizing the recent advances made in the research field of cyclic aryliodoniums, including the nascent design of aryliodonium species and their synthetic applications. First, the general preparation of typical diphenyl iodoniums is described, followed by the construction of heterocyclic iodoniums and monoaryl iodoniums. Then, the initiated arylations coupled with subsequent domino reactions are summarized to construct polycycles. Meanwhile, the advances in cyclic aryliodoniums for building biaryls including axial atropisomers are discussed in a systematic manner. Finally, a very recent advance of cyclic aryliodoniums employed as halogen-bonding organocatalysts is described.

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“…This leads to tremendous distinctions in the structure and properties of BINOLs. However, only a few examples combine both C–O coupling and dearomatization for this skeleton . Furthermore, studies linking the subsequent tandem reactions, especially all-carbon ring formation reactions, have not yet been reported .…”

mentioning

confidence: 99%

C–O Coupling/[4+2] Cycloaddition Tandem Reactions via Oxidative Dearomatization of BINOLs: Access to Bridged Polycyclic Compounds

et al. 2023

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Intramolecular C−H activation/C−O coupling, dearomatization, and [4+2] cycloaddition of BINOL units have been well developed in a one-pot approach with maleimide derivatives as the dienophiles. This tandem catalytic system generates a variety of functionalized bridged polycyclic products in a step-economical manner, which greatly enriches the modification methods and strategies for the BINOL skeletons.

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Oxidation of BINOLs by Hypervalent Iodine Reagents: Facile Synthesis of Xanthenes and Lactones

Cited by 9 publications

References 81 publications

Regioselective Substitution of BINOL

Regioselective Substitution of BINOL

Recent Progress in Cyclic Aryliodonium Chemistry: Syntheses and Applications

C–O Coupling/[4+2] Cycloaddition Tandem Reactions via Oxidative Dearomatization of BINOLs: Access to Bridged Polycyclic Compounds

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