Application Progress of Silyl Carboxylic Acid in Organic Synthesis

doi:10.6023/cjoc202303030

Abstract

Carboxylic acids play important roles in basic life processes within organisms, and are powerful building blocks in the field of organic synthesis. Therefore, natural or artificial carboxylic acids have been studied from a variety of viewpoints. Silyl carboxylic acids, as analogues of carboxylic acids, are highly attractive due to their unique physical and chemical properties as well as their potential reactivity. The applications of silyl carboxylic acids in the carbonyl coupling reactions, silyl radical reactions and esterification are summarized.

Key words: silyl carboxylic acid, carbon monoxide, carbonylation reaction, silyl radical precursor

Cite this article

Guangqing Guo, Zhong Lian. Application Progress of Silyl Carboxylic Acid in Organic Synthesis[J]. Chinese Journal of Organic Chemistry, 2023, 43(10): 3580-3589.

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Fig. & Tab. 21

Scheme 1. Applications of silyl carboxylic acid in the organic synthesis chemistry

Scheme 2. Discovery and synthesis of silicic acid

Scheme 3. Mechanism of CO release from silicic acid

Scheme 4. Carbonylation reactions using silicic acid as a CO precursor

Scheme 5. Synthesis of aromatic carboxylic acids from aryl halides and silicic acids

Scheme 6. Synthesis of amides from aryl halides and silicic acid

Scheme 7. Carbonylation coupling of aryl halides/vinyl halides

Scheme 8. Synthesis of indigoidin from 2-iodoaniline with silicic acid

Scheme 9. Synthesis of amides from the reaction between silicic acid, aryl iodide and amino acid/peptide nucleophile

Scheme 10. Synthesis of amides from the reaction between alkyl zinc reagents, fatty amines and silicic acid

Scheme 11. Alkene hydroacylation reaction involving silicic acid

Scheme 12. Synthesis of radioactive drug molecules with CO released from silicic acid

Scheme 13. Tracer synthesis with CO released from silicic acid

Scheme 14. Synthesis of tracer with CO released from silicic acid and Pd(II) complex

Scheme 15. Tracer synthesis by using α,α-dimethylbenzylamine

Scheme 16. Synthesis of diaryl ketones with silicic acid

Scheme 17. Synthesis of indolone with silicic acid

Scheme 18. Synthesis of iron complexes with silicic acid

Scheme 19. Silicic acid used for the bifunctionalization of olefin

Scheme 20. Esterification of silicic acid with alcohol

Scheme 21. Esterification of silicic acid with aryl iodide

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