Palladium-catalysed reactions of 6-halogeno-1,1′-binaphthyl derivatives. A detailed investigation of structure/reactivity and structure/selectivity relationships

Fehér, Csaba; Urbán, Béla; Ürge, László; Darvas, Ferenç; Bakos, József; Skoda‐Földes, Rita

doi:10.1016/j.tet.2011.06.011

Cited by 4 publications

(3 citation statements)

References 28 publications

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“…Introducing an O ‐bound Boc group provided carbonate 16c . It was our first type 16 substrate to react with NBS/DMF as expected . Bromonaphthalene 14c resulted in 94 % yield as a single isomer, that is, without a trace of the regioisomer iso ‐ 14c…”

Section: Introductionmentioning

confidence: 66%

“…This approach defined type 14 naphthyl halides as desirable precursors. While not described in the literature, they looked accessible by brominating or iodinating type 16 naphthalenes. An attractive way of getting hold of such substrates seemed to be the Diels–Alder reaction of an aryne 17 oxygenated at C‐3 and C‐4 (PG′′ being a protective group) with a furan oxygenated at C‐2 (PG′′′ being another protective group).…”

Section: Introductionmentioning

confidence: 99%

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Establishing Consensus Stereostructures for the Naphthoquinonopyrano‐γ‐lactone Natural Products (–)‐Arizonin B1 and (–)‐Arizonin C1 by Total Syntheses. Diastereocontrol of Oxa‐Pictet–Spengler Cyclizations by Protective‐Group Optimization

Neumeyer

Brückner

2017

Eur J Org Chem

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Previous total syntheses of arizonin C1 (4) led to opposite assignments of its absolute configuration. Here, we report the fourth total synthesis thereof. In addition, we disclose the first total synthesis of arizonin B1 (3) proceeding differently than via arizonin C1. The stereocenters of the two targets stemmed from an asymmetric dihydroxylation and an ensuing oxa‐Pictet–Spengler cyclization. Their configurations were in line with Fernandes' assignments. Protective‐group variation in the substrate modulated the diastereoselectivity of the Pictet–Spengler cyclization between 77:23 in favor of a trans disubstitution at C‐3a vs. C‐5 – used for preparing the natural (–)‐arizonins C1 and B1 – and 100:0 in favor of a cis disubstitution – exploited for synthesizing the unnatural (+)‐5‐epi‐arizonins C1 and B1. All naphthalenes of the present study were derived from the (benzyloxy)methoxynaphthalenediol 19. It resulted from a Diels–Alder reaction of the aryne 17a with the siloxyfuran 18a.

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Section: Introductionmentioning

confidence: 66%

Section: Introductionmentioning

confidence: 99%

Establishing Consensus Stereostructures for the Naphthoquinonopyrano‐γ‐lactone Natural Products (–)‐Arizonin B1 and (–)‐Arizonin C1 by Total Syntheses. Diastereocontrol of Oxa‐Pictet–Spengler Cyclizations by Protective‐Group Optimization

Neumeyer

Brückner

2017

Eur J Org Chem

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“…120 When BINOL monopivalate 26 was treated with Ag 2 SO 4 and I 2 in ethanol at room temperature, the 6-iodo product 34 was obtained in 95% yield (Scheme 7). 121,122 This compound led to the synthesis of a variety of 6-substituted BINOL derivatives via transition metal-catalyzed cross-coupling reactions and showed better reactivity than the corresponding bromo analogues.…”

Section: Iodonationmentioning

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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A Half Century of the Sonogashira Reaction

Frankenberger,

Wendinger,

Scherer

et al. 2025

Organic Reactions

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Conjugated alkynes are valuable intermediates in the synthesis of natural products, agrochemicals, pharmaceuticals, fine chemicals, and organic molecular materials. Since its introduction in 1975, the palladium‐catalyzed Sonogashira reaction has become the primary choice for the construction of sp–sp 2 carbon–carbon bonds in aryl‐, heteroaryl‐, and alkenyl‐substituted alkynes. A vast range of reaction conditions have been explored to expand and optimize the scope of the Sonogashira reaction, including sustainable variants, microwave‐assisted cross couplings, and cross couplings performed in water. Research efforts also target the development of improved catalytic systems for the Sonogashira reaction, such as solid‐supported palladium catalysts and nanoparticles, the use of N ‐heterocyclic carbenes (NHCs) as ligands, as well as copper‐free variants of the reaction. This Chapter reviews the application of the palladium‐catalyzed Sonogashira cross coupling of terminal alkynes with aryl or alkenyl halides and triflates. Coupling reactions that form conjugated alkynes via alternative methods, or use different electrophiles, catalysts, or alkynes, are also briefly described.

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Palladium-catalysed reactions of 6-halogeno-1,1′-binaphthyl derivatives. A detailed investigation of structure/reactivity and structure/selectivity relationships

Cited by 4 publications

References 28 publications

Establishing Consensus Stereostructures for the Naphthoquinonopyrano‐γ‐lactone Natural Products (–)‐Arizonin B1 and (–)‐Arizonin C1 by Total Syntheses. Diastereocontrol of Oxa‐Pictet–Spengler Cyclizations by Protective‐Group Optimization

Establishing Consensus Stereostructures for the Naphthoquinonopyrano‐γ‐lactone Natural Products (–)‐Arizonin B1 and (–)‐Arizonin C1 by Total Syntheses. Diastereocontrol of Oxa‐Pictet–Spengler Cyclizations by Protective‐Group Optimization

Regioselective Substitution of BINOL

A Half Century of the Sonogashira Reaction

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