Palladium-Catalyzed Formation of Aryl <i>tert</i>-Butyl Ethers from Unactivated Aryl Halides

Parrish, Cynthia A.; Buchwald, Stephen L.

doi:10.1021/jo001426z

Cited by 110 publications

(45 citation statements)

References 22 publications

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“…63 With those ligands, especially biphenyl-based ligands, low catalyst loadings and lower reaction temperature were feasible to convert various halides in good to excellent yields.…”

Section: Formation Of Aryl Alkyl Ethers-transformation Of Aryl Halidesmentioning

confidence: 99%

Palladium-catalysed hydroxylation and alkoxylation

2011

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The formation of oxygen-carbon bonds is one of the fundamental transformations in organic synthesis. In this regard the application of palladium-based catalysts has been extensively studied during recent years. Nowadays it is an established methodology and the success has been proven in manifold synthetic procedures. This tutorial review summarizes the advances on palladiumcatalysed C-O bond formation, means hydroxylation and alkoxylation reactions.

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“…63 With those ligands, especially biphenyl-based ligands, low catalyst loadings and lower reaction temperature were feasible to convert various halides in good to excellent yields.…”

Section: Formation Of Aryl Alkyl Ethers-transformation Of Aryl Halidesmentioning

confidence: 99%

Palladium-catalysed hydroxylation and alkoxylation

2011

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“…1-tert-Butoxyoctane [4] (1a) 2-tert-butoxy-octane [4] (1b), (1S,2R,4R)-2-tert-butoxy-1-isopropyl-4-methylcyclohexane [4] (1c) 2-tert-butoxy-1,2-diphenylethanone [4] (1e), 1-tert-butoxynon-3-ene [4] (1f), (S)-ethyl 2-tert-butoxypropanoate [17] (1h), 1-tert-butoxybenzene [4] (1i), 1-tert-butoxynaphthalene [4] (1j), 2-tert-butoxynaphthalene [4] (1k), 1-tert-butoxy-4-methoxybenzene [18] (1m) 1-tert-butoxy-4-nitrobenzene [19] (1p), 1-tert-butoxy-4-fluorobenzene [4] (1q), 1-tert-butoxy-3-chlorobenzene [4] (1r) are completely characterized known compounds.…”

Section: Preparation Of the Starting Materials: Synthesis Of Tertbutymentioning

confidence: 99%

tert‐Butyl Ethers: Renaissance of an Alcohol Protecting Group. Facile Cleavage with Cerium(III) Chloride/Sodium Iodide

et al. 2006

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The tert-butoxy derivative is one of the most underused alcohol protecting groups. After having developed an easy and useful protocol for its introduction, we offer here a simple procedure for its removal by treatment with anhydrous CeCl 3 and NaI in CH 3 CN. The procedure led to the successful cleavage of aliphatic and aromatic tert-butyl ethers and was compatible with various other functionalities and protecting groups present in the molecule.

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“…The remaining Cl functionality in 6 l and 6 g was subjected to palladium-catalyzed CÀN or CÀO coupling reactions [17,18] to introduce nitrogen or oxygen functionality. Thus, aniline 8 and phenyl ether 9 were isolated in 83 % and 52 % yields, respectively.…”

Section: Xinyu Liu Masaki Shimizu* and Tamejiro Hiyamamentioning

confidence: 99%

A Facile Stereocontrolled Approach to CF₃‐Substituted Triarylethenes: Synthesis of Panomifene

2004

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Palladium-Catalyzed Formation of Aryl tert-Butyl Ethers from Unactivated Aryl Halides

Cited by 110 publications

References 22 publications

Palladium-catalysed hydroxylation and alkoxylation

Palladium-catalysed hydroxylation and alkoxylation

tert‐Butyl Ethers: Renaissance of an Alcohol Protecting Group. Facile Cleavage with Cerium(III) Chloride/Sodium Iodide

A Facile Stereocontrolled Approach to CF₃‐Substituted Triarylethenes: Synthesis of Panomifene

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Palladium-Catalyzed Formation of Aryl tert-Butyl Ethers from Unactivated Aryl Halides

Cited by 110 publications

References 22 publications

Palladium-catalysed hydroxylation and alkoxylation

Palladium-catalysed hydroxylation and alkoxylation

tert‐Butyl Ethers: Renaissance of an Alcohol Protecting Group. Facile Cleavage with Cerium(III) Chloride/Sodium Iodide

A Facile Stereocontrolled Approach to CF3‐Substituted Triarylethenes: Synthesis of Panomifene

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A Facile Stereocontrolled Approach to CF₃‐Substituted Triarylethenes: Synthesis of Panomifene