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Multikilogram-Scale Synthesis of a Biphenyl Carboxylic Acid Derivative Using a Pd/C-Mediated Suzuki Coupling Approach

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TLDR
In this article, NaOH is added to a mixture of 4-bromo-3-methylaniline, 4-chlorobutyryl chloride, and catalytic TBAC in THF/H2O.
About
This article is published in Organic Process Research & Development.The article was published on 1999-05-21. It has received 110 citations till now. The article focuses on the topics: Yield (chemistry) & Suzuki reaction.

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Citations
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Organic Reactions in Aqueous Media with a Focus on Carbon−Carbon Bond Formations: A Decade Update

TL;DR: Reaction of R,â-Unsaturated Carbonyl Compounds 3127: Reaction of R-UnSaturated Carbonies 3127 7.1.6.
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Carbon-Carbon Coupling Reactions Catalyzed by Heterogeneous Palladium Catalysts

TL;DR: Pd on Modified Silica 159 4.5.1.
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Large-Scale Applications of Amide Coupling Reagents for the Synthesis of Pharmaceuticals

TL;DR: In this article, a review of coupling reagents for large-scale amide synthesis via the condensation of an acid and amine is presented, highlighting the benefits and drawbacks of each reagent on an industrial scale.
References
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Journal ArticleDOI

The Palladium-Catalyzed Cross-Coupling Reaction of Phenylboronic Acid with Haloarenes in the Presence of Bases

TL;DR: The transition metal-catalyzed reactions of organometallics with organic halides have been extensively studied to prove a new approach to selective formation of carbon-carbon bonds as mentioned in this paper.
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New synthetic transformations via organoboron compounds

TL;DR: In this paper, the palladium-catalyzed cross-coupling reaction of 1-alkenylboron compounds with various vinylic or aryl halides in the presence of base provides the corresponding coupling products.
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Highly Efficient and Accelerated Suzuki Aryl Couplings Mediated by Phosphine-Free Palladium Sources

TL;DR: The phosphine-free methodology appears to be generally applicable; cross-couplings of aryl iodides yielding biaryls 6 and 7 proceed without noticeable steric or electronic effects.
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Aryl couplings with heterogeneous palladium catalysts

TL;DR: The coupling reaction of diverse phenylboronic acids with aryl halogenides and triflates has been performed by the use of simple palladium hydrogenation catalysts as discussed by the authors.
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