Formylation

Common Conditions:

Lithiation

Lithiation followed by electrophilic quench with DMF is a common method for formylation. Lithiation of substrates is typically carried out by organolithiums (ex. n-BuLi, s-BuLi, or t-BuLi) or a hindered lithium amide base (ex. LDA).

Examples

Lithium-Halogen Exchange

Lithium-Halogen exchange followed by electrophilic quench with DMF is a common method for formylation.

Examples

Rieche Formylation

Rieche formylation uses dichloromethyl methyl ether to formylate aromatic rings in the presence of a Lewis acid catalyst (ex. TiCl4, SnCl4, or AlCl3).^[1][2]

Examples

Reaction Map:

The reaction map is intended to provide insight into possible reactions one step before and after the title reaction. It also serves as an alternative way to navigate the website, and as a means of coming up with retrosynthetic ideas. Click on the reaction arrow to visit the page.

References:

1) Carey, F. A.; Sundberg, R. J.; Advanced Organic Chemistry, Part B: Reactions and Synthesis, 5th Edition

2) Smith, M. B.; March's Advanced Organic Chemistry, 7th Edition