A General and Efficient Catalyst for Palladium-Catalyzed C−O Coupling Reactions of Aryl Halides with Primary Alcohols

Gowrisankar, Saravanan; Sergeev, Alexey G.; Anbarasan, Pazhamalai; Spannenberg, Anke; Neumann, Helfried; Beller, Matthias

doi:10.1021/ja103248d

Cited by 222 publications

(119 citation statements)

References 79 publications

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“…The secondary alcohol was chosen as a substrate that currently represents a challenge in transition metal-catalyzed alkyl-aryl ether bond forming reactions due to competitive oxidation to ketone byproducts. 6,7 Therefore, success using this class of alcohol would constitute a general advance in strategy for assembling these molecules. Empirical screening of reaction conditions led to the "standard conditions" in Table 1, entry 1.…”

Section: ■ Introductionmentioning

confidence: 99%

Base Mediated Synthesis of Alkyl-aryl Ethers from the Reaction of Aliphatic Alcohols and Unsymmetric Diaryliodonium Salts

Sundalam

Stuart

2015

J. Org. Chem.

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The base mediated coupling of aliphatic alcohol pronucleophiles with unsymmetric diaryliodonium salt electrophiles is described. This metal-free reaction is operationally simple, proceeds at mild temperature, and displays broad substrate scope to generate industrially important alkyl-aryl ethers in moderate to excellent yield. The synthetic utility of these reactions is demonstrated, and aspects of sustainability are highlighted by the use of unsymmetric aryl(mesityl)iodonium arylating reagents.

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Section: ■ Introductionmentioning

confidence: 99%

Base Mediated Synthesis of Alkyl-aryl Ethers from the Reaction of Aliphatic Alcohols and Unsymmetric Diaryliodonium Salts

Sundalam

Stuart

2015

J. Org. Chem.

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“…The Buchwald-Hartwig coupling reaction was applied to attach diverse (di)aza(bi)cyclic scaffolds to compounds 16a–c (Scheme 2). 43 Various ligands, bases, catalysts and solvents are described for this coupling in the literature. 44–49 For our reactions, highest yields were achieved using R,S-BINAP and XPhos.…”

Section: Resultsmentioning

confidence: 99%

The twin drug approach for novel nicotinic acetylcholine receptor ligands

Tomassoli

Gündisch

2015

Bioorganic & Medicinal Chemistry

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The association of two pharmacophoric entities generates so-called “twin drugs” or dimer derivatives. We applied this approach for the design of a small compound library for the interaction with α4β2* nicotinic acetylcholine receptors (nAChRs). In this compound series, the nAChR ligand N,N-dimethyl-2-(pyridin-3-yloxy)ethan-1-amine 9 served as one pharmacological entity and it was initially kept constant as one part of the “twin” compound. “Twin” compounds with identical or non-identical entities using the “no linker mode” or “overlap” mode were synthesized and evaluated for their nAChR affinities. Compound 17a showed the highest affinity for the α4β2* nAChR subtype (Ki = 0.188 nM) and its (di)fluoro analogs could retain nanomolar affinities, when replacing pyridine as the hydrogen bond acceptor system by mono- or difluoro-phenyls. The “twin drug” approach proved to provide compounds with high affinity and subtype selectivity for α4β2* nAChRs.

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“…In large part due to the success of palladium-catalyzed arene cross-coupling reactions between carbon and a wide variety of other atoms -in particular B [88,89], C [84,90], N [91][92][93][94], and O [95,96] -Pd-mediated and Pd-catalyzed arene fluorination has been targeted as a promising approach. Early work in this field was primarily led by Grushin, who began exploring the synthesis and reactivity of the first mononuclear arylpalladium (II) fluoride complexes (Fig.…”

Section: Nucleophilic Arene Fluorinationmentioning

confidence: 99%

Transition Metal-Mediated and Metal-Catalyzed Carbon–Fluorine Bond Formation

Campbell

Hoover

Ritter

2014

Topics in Organometallic Chemistry

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The development of new C-F bond forming reactions from organotransition metal complexes has played a key role in advancing the field of fluorination chemistry and has allowed for improved access to fluorinated organic molecules of interest in medicine, materials, and agrochemicals. In this review, we describe the development of transition metal-mediated and metal-catalyzed fluorination methods over the past decade. Special attention is paid to the variety of organometallic mechanisms by which C-F bond formation can occur and the strengths and limitations of different approaches.

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A General and Efficient Catalyst for Palladium-Catalyzed C−O Coupling Reactions of Aryl Halides with Primary Alcohols

Cited by 222 publications

References 79 publications

Base Mediated Synthesis of Alkyl-aryl Ethers from the Reaction of Aliphatic Alcohols and Unsymmetric Diaryliodonium Salts

Base Mediated Synthesis of Alkyl-aryl Ethers from the Reaction of Aliphatic Alcohols and Unsymmetric Diaryliodonium Salts

The twin drug approach for novel nicotinic acetylcholine receptor ligands

Transition Metal-Mediated and Metal-Catalyzed Carbon–Fluorine Bond Formation

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