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Concept
Formylation
Summary
Formylation refers to any chemical processes in which a compound is functionalized with a formyl group (-CH=O). In organic chemistry, the term is most commonly used with regards to aromatic compounds (for example the conversion of benzene to benzaldehyde in the Gattermann–Koch reaction). In biochemistry the reaction is catalysed by enzymes such as formyltransferases.
Formylation generally involves the use of formylation agents, reagents that give rise to the CHO group. Among the many formylation reagents, particularly important are formic acid and carbon monoxide. A formylation reaction in organic chemistry refers to organic reactions in which an organic compound is functionalized with a formyl group (-CH=O). The reaction is a route to aldehydes (C-CH=O), formamides (N-CH=O), and formate esters (O-CH=O).
A reagent that delivers the formyl group is called a formylating agent.
Formic acid
Dimethylformamide and phosphorus oxychloride in the Vilsmeier-Haack reaction.
Hexamethylenetetramine in the Duff reaction and the Sommelet reaction
Carbon monoxide and hydrochloric acid in the Gattermann-Koch reaction
Cyanides in the Gattermann reaction. This method synthesizes aromatic aldehydes using hydrogen chloride and hydrogen cyanide (or another metallic cyanide as such zinc cyanide) in the presence of Lewis acid catalysts:
Chloroform in the Reimer-Tiemann reaction
Dichloromethyl methyl ether in Rieche formylation.
A particularly important formylation process is hydroformylation, which converts alkenes to the homologated aldehyde.
Formylation reactions are a form of electrophilic aromatic substitution and therefore work best when the aromatic starting materials are electron-rich. Phenols are very commonly encountered as they can be readily deprotonated to form phenoxides which are excellent nucleophiles, other electron rich substrates such as mesitylene, pyrrole, or fused aromatic rings can also be expected to react. Benzene will react under aggressive conditions but deactivated rings such as pyridine are difficult to formylate effectively.
Official source
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