Cascade Alkenylation/Intramolecular Friedel–Crafts Alkylation: High Selectivity at the C7-Position of BINOL

Líu, Hao; Gong, Zi-Rong; Zhao, Yu; Zheng, Jing; Yong, Xu; Dong, Lin

doi:10.1021/acs.joc.3c00537

Cited by 8 publications

(2 citation statements)

References 47 publications

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“…As shown in Scheme 134 (vide infra), the 6-pyrazole group of BINOL can direct the Co-catalyzed C−H activation at the less sterically hindered 7-position to form the product 390. 345 The pyrazole group of 390 was found to further direct a C−H activation at the 5-position upon Rh(III) catalysis (Scheme 129). In the presence of 5…”

Section: Rh-catalyzed Reactions At 3- 4- and 5-positionsmentioning

confidence: 99%

“…It was found that an In 2023, Liu et al reported the use of a 6-pyrazole group to direct a C−H activation at the 7-position of BINOL by using the Co(III) catalyst 370 (Scheme 134). 345 Compound 388 was synthesized from the reaction of 6-bromoBINOL with pyrazole in the presence of Cu 2 O and K 2 CO 3 in DMSO at 130 °C over 2 d under argon. Significant racemization of BINOL was observed in this step.…”

Section: Co-catalyzed Reactions At 3-and 7-positionsmentioning

confidence: 99%

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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: Rh-catalyzed Reactions At 3- 4- and 5-positionsmentioning

confidence: 99%

Section: Co-catalyzed Reactions At 3-and 7-positionsmentioning

confidence: 99%

Regioselective Substitution of BINOL

2024

Chem. Rev.

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Rh(III)‐Catalyzed Annulative Coupling of Sulfoxonium Ylides with Allyl Acetates: Generation of Bicyclo[4.1.0]heptan‐2‐ones

et al. 2023

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The Construction of Novel Spirocyclic Frameworks with Cyclobutane through Rh(III)-Catalyzed [3 + 2]-Annulation between Quinoxalines and Alkynylcyclobutanols

Gang,

Dong

2024

J. Org. Chem.

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An effective synthesis strategy for the preparation of 1′Hspiro[indene-1,2′-quinoxaline] has been developed. This involves a Rh(III)-catalyzed [3 + 2]-annulation of quinoxalines with alkynylcyclobutanols. The developed protocol offers a straightforward method for the preparation of versatile heterocyclic compounds with a four-membered ring and is compatible with a wide range of functional groups.

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Cascade Alkenylation/Intramolecular Friedel–Crafts Alkylation: High Selectivity at the C7-Position of BINOL

Cited by 8 publications

References 47 publications

Regioselective Substitution of BINOL

Regioselective Substitution of BINOL

Rh(III)‐Catalyzed Annulative Coupling of Sulfoxonium Ylides with Allyl Acetates: Generation of Bicyclo[4.1.0]heptan‐2‐ones

The Construction of Novel Spirocyclic Frameworks with Cyclobutane through Rh(III)-Catalyzed [3 + 2]-Annulation between Quinoxalines and Alkynylcyclobutanols

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