Chemoselective Synthesis of Carbonyl Compounds

Chemoselective synthesis of carbonyl compounds encompasses a suite of strategies that target the formation or modification of aldehydes and ketones in the presence of other reactive functionalities. Central to this field are approaches that exploit protecting‐group chemistry, organometallic intermediates and catalytic activation to achieve high selectivity and functional‐group tolerance. Key tactics include the use of dithioacetal derivatives as masked acyl anion equivalents, enabling selective carbon–carbon bond formation and subsequent deprotection to release the carbonyl functionality. Advances in milder reagents and one‐pot protocols have enhanced atom economy and operational simplicity, meeting the growing demand for sustainable processes. The resulting methods underpin the synthesis of fine chemicals, pharmaceuticals and complex natural products by allowing precise introduction of the carbonyl moiety without over‐reduction or side‐reactions. Contemporary research places particular emphasis on environmentally benign reagents, solvent‐free conditions and catalytic systems that deliver unparalleled chemoselectivity under ambient or near‐ambient temperatures.

Research from Nature Portfolio

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Chemoselective Synthesis of Carbonyl Compounds publication trend

The graph below shows the total number of articles in chemoselective synthesis of carbonyl compounds across all publications each year (not limited to Nature Index journals).

Technical terms

Chemoselectivity: The preferential reaction of a reagent with one functional group in a molecule containing multiple reactive sites.

Carbonyl compound: An organic molecule featuring a carbon-oxygen double bond, such as an aldehyde or ketone, central to numerous synthetic transformations.

Thioacetal: A functional group in which a carbonyl has been converted into a dithioacetal by reaction with thiols, used to protect or mask the carbonyl functionality.

Dithiane: A six-membered ring containing two sulfur atoms that serves as a stable acyl anion equivalent in chemoselective bond‐forming reactions.

β-Sulfanyl ketone: A ketone bearing a sulfur substituent at the β-position, often accessed via thioacetal rearrangement or thia-Michael addition under chemoselective conditions.

References

1. The Corey-Seebach Reagent in the 21st Century: A Review. Molecules (2023).
2. Controllable Synthesis of Thioacetals/Thioketals and β-Sulfanyl Ketones Mediated by Methanesulfonic Anhydride and Sulfuric Acid Sulfuric Acid from Aldehyde/Acetone and Thiols. Molecules (2024).
3. Pot-Economy Autooxidative Condensation of 2‑Aryl-2-lithio-1,3-dithianes. The Journal of Organic Chemistry (2018).