Ch. 16 - Metals in Organic Chemistry

Mullins - Organic Chemistry: A Learner Centered Approach 1st Edition

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Mullins 1st Edition

Ch. 16 - Metals in Organic Chemistry

Problem 33b

Chapter 15, Problem 33b

Predict the product of the diorganocuprate cross-coupling reactions shown.
(b)

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Identify the reactants involved in the diorganocuprate cross-coupling reaction. Typically, this involves an organohalide and a diorganocuprate reagent, such as R2CuLi.

Understand the role of the diorganocuprate reagent. In this reaction, the diorganocuprate (R2CuLi) acts as a nucleophile, where one of the R groups will replace the halide (X) on the organohalide (R'-X).

Determine which R group from the diorganocuprate will participate in the coupling. Generally, one of the R groups will transfer to the organohalide, forming a new carbon-carbon bond.

Predict the product by replacing the halide (X) on the organohalide with the R group from the diorganocuprate. The resulting product will be R'-R, where R' is the original organic group from the organohalide.

Consider any stereochemical or regiochemical outcomes if applicable. In many cases, the reaction proceeds with retention of configuration, but it's important to verify based on the specific reactants involved.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Diorganocuprate Reagents

Diorganocuprate reagents, typically denoted as R2CuLi, are organocopper compounds used in organic synthesis for cross-coupling reactions. They are formed by reacting organolithium compounds with copper(I) salts. These reagents are known for their ability to couple with organic halides, forming new carbon-carbon bonds, which is crucial in predicting the products of such reactions.

Cross-Coupling Reaction Mechanism

Cross-coupling reactions involve the formation of a new carbon-carbon bond between two different organic groups. In the context of diorganocuprate reactions, the mechanism typically involves oxidative addition of the organic halide to the copper center, followed by reductive elimination to form the coupled product. Understanding this mechanism is essential for predicting the outcome of the reaction.

Regioselectivity in Coupling Reactions

Regioselectivity refers to the preference for the formation of one constitutional isomer over another in a chemical reaction. In diorganocuprate cross-coupling reactions, regioselectivity is influenced by the nature of the organic groups and the halide involved. Recognizing how these factors affect the position and type of the new bond formed is key to accurately predicting the product structure.

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Sonogashira Coupling Reaction

Related Practice

Textbook Question

Based on the stereochemical result alone, how can you tell that this reaction does not proceed by an Sₙ2 mechanism?

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Textbook Question

Predict the product of the following Sonogashira coupling reactions.

(b)

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Textbook Question

The trimethylsilyl (TMS) group, used as a protecting group for alcohols, can also be used a protecting group for terminal alkynes. Show how TMS-acetylene could be used to link together two aryl halides using the Sonogashira reaction. [Hint: Deprotection of the TMS-acetylene can be done using KF in H₂O.]

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Textbook Question

Predict the product of the diorganocuprate cross-coupling reactions shown.

(a)

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Textbook Question

Predict the product of the diorganocuprate cross-coupling reactions shown.

(c)

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