- Practical Ligand-Free Copper-Catalysed Short-Chain Alkoxylation of Unactivated Aryl Bromides
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An efficient and practical short-chain alkoxylation of unactivated aryl bromides has been developed with special attention focussed on the applicability of the reaction. Sodium alkoxide is used as the nucleophile, and the corresponding alcohol as the solvent. The reaction requires neither precious metals nor organic ligands. It uses a catalytic system consisting of copper(I) bromide as a catalyst, the corresponding alkyl formate as a noncontaminating cocatalyst, and lithium chloride as an additive. A wide range of substrates and test cases highlight the synthetic utility of the approach. Considering the commercial accessibility and affordability of the feedstocks, this protocol shows promise as a new alternative for the sustainable preparation of aryl alkyl ethers.
- Guo, Ying,Fan, Xue-Min,Nie, Min,Liu, Hong-Wei,Liao, Dao-Hua,Pan, Xian-Dao,Ji, Ya-Fei
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p. 4744 - 4755
(2015/08/03)
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- Synthesis of aryl ethers from benzoates through carboxylate-directed C-H-activating alkoxylation with concomitant protodecarboxylation
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One in, one out: In the presence of a copper/silver bimetallic catalyst system, aromatic carboxylate salts undergo ortho C-H alkoxylation with concomitant loss of the carboxylate directing group in a protodecarboxylation step (see scheme, FG=functional group). This process provides a convenient synthetic access to the important class of aromatic ethers from widely available carboxylic acids. Copyright
- Bhadra, Sukalyan,Dzik, Wojciech I.,Goo?en, Lukas J.
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p. 2959 - 2962
(2013/04/10)
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- Synthesis of aryl ethers from aromatic carboxylic acids
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A silver/copper bimetallic catalyst system promotes the decarboxylative Chan-Evans-Lam alkoxylation of ortho-substituted aromatic carboxylate salts with tetraalkyl orthosilicates or triaryl borates. Non-ortho-substituted carboxylates are alkoxylated via an ortho-C-H-alkoxylation with concomitant cleavage of the carboxylate directing group via protodecarboxylation. This way, meta-substituted carboxylates are converted into para-substituted alkoxyarenes and vice versa. The combined processes provide a convenient synthetic entry to the important class of aromatic ethers from widely available carboxylic acids.
- Bhadra, Sukalyan,Dzik, Wojciech I.,Goossen, Lukas J.
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supporting information
p. 2387 - 2390
(2013/09/23)
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- COMPOUNDS AND METHODS USEFUL FOR TREATING ASTHMA AND ALLERGIC INFLAMMATION
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Compounds, compositions and methods that are useful in the treatment of inflammatory and immune-related diseases and conditions are provided herein. In particular, the invention provides compounds which modulate the function and/or expression of proteins involved in atopic diseases, inflammatory conditions and cancer. The subject compounds are carboxylic acid derivatives.
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Page/Page column 72
(2009/01/20)
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- One-step preparation of some 3-substituted anisoles
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A one-step preparation of 3-bromoanisole, 3-chloroanisole, and 3-trifluoromethylanisole from the corresponding 3-substituted nitrobenzenes is carried out by nucleophilic aromatic substitution of the nitro group with sodium or potassium methoxide, employing an effective amount of a phase-transfer catalyst (PTC), in a medium of a nonpolar aprotic solvent, under aerobic conditions, at a temperature of 50-65°C. The alkali methoxide used can be a pre-prepared solid, or it can be prepared in situ from the alkali hydroxide and methanol. The methoxydenitration proved to be very sensitive to the type of PTC. The effect of the solvent on the reaction is discussed. The targeted anisoles are obtained in yields of more than 80% and purities of greater than 99%.
- Zilberman, Joseph
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p. 303 - 305
(2013/09/06)
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