Chapter 29: Problem 3

Discuss the synthetic uses of organometallic compounds of boron.

Short Answer

Expert verified

Organometallic compounds of boron, notably boranes and borohydrides, are widely used in synthetic chemistry for their reducing properties, participation in Suzuki cross-coupling reactions and usage in hydroboration to produce organoboranes.

Step by step solution

- Introduction to Organometallic Compounds of Boron

Organometallic compounds of boron, such as boranes and borohydrides, exhibit interesting chemical behaviors due to their electron deficiency, making them valuable in synthetic chemistry. One of the most common organoboron compounds used in synthetic chemistry is Borane (BH3), a reactive compound known for its reducing properties.

- Borohydrides as Reducing Agents

Borohydrides like sodium borohydride (NaBH4) and lithium aluminium borohydride (LiAlH4) are widely used reducing agents in organic chemistry. They are used for the reduction of carbonyl compounds to alcohols. Lithium aluminium borohydride is even strong enough to reduce carboxylic acids and esters to alcohols.

- Boronic Acids in Suzuki Coupling

Another significant use of organoboron compounds in synthetic chemistry is found in cross-coupling reactions, specifically in the Suzuki reaction. Boronic acids and their derivatives participate in palladium-catalyzed cross-coupling reactions with aryl halides or vinyl halides to give corresponding aryl-aryl or aryl-vinyl compounds. This method is valuable for forming carbon-carbon bonds.

- Hydroboration

Hydroboration is another industrial synthesis that uses diborane (B2H6). In this reaction, an alkene reacts with diborane to produce organoboranes, which can be further oxidized to produce alcohols. The hydroboration reaction is stereospecific, taking place with syn stereochemistry, which allows for control over the stereochemistry of the products and has broad applications in the synthesis of complex molecules.

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Discuss the synthetic uses of organometallic compounds of boron.

Short Answer

Step by step solution

- Introduction to Organometallic Compounds of Boron

- Borohydrides as Reducing Agents

- Boronic Acids in Suzuki Coupling

- Hydroboration

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