Synthesis of Aldehydes, Ketones, and Carboxylic Acids from Lower Carbonyl Compounds by C-C Coupling Reactions

The methodology for the preparation of aldehydes, ketones, and carboxylic acids or their derivatives from lower carbonyl compounds by carbon-carbon bond forming reactions is reviewed. The material is presented according to the number of carbon atoms (1, 2, 3, or 4) that separate the carbonyl or acyl group, added during the carbon-carbon bond formation, from the original electrophilic center. 1. Introduction 2. Aldehydes and Ketones by One Carbon Elongations 2.1. Addition of Masked Acyl Anions 2.2. Reductive Nucleophilic Acylation 2.3. Nucleophilic Acylation Followed by Additional Carbonyl Elaboration 3. Carboxylic Acids or Their Derivatives by One Carbon Elongations 3.1. Addition of Masked Carboxyl Anions 3.2. Reductive Nucleophilic Carboxylation 3.3. Nucleophilic Carboxylation Followed by Additional Carbonyl Elaboration 4. Aldehydes and Ketones by Two Carbon Elongations 4.1. Aldol Condensation and Related Reactions 4.2. Wittig and Other Olefination Reactions 5. Carboxylic Acids or Their Derivatives by Two Carbon Elongations 5.1. Addition of Enolates of Carboxylic Acid Derivatives 5.2. Reaction with Ketene and Related Compounds 5.3. Wittig and Other Olefination Reactions 6. Three Carbon Elongations 6.1. Synthesis of Aldehydes and Ketones 6.2. Synthesis of Carboxylic Acids and Derivatives 7. Four Carbon Elongations 7.1. Synthesis of Aldehydes and Ketones 7.2. Synthesis of Carboxylic Acids and Derivatives 8. Conclusions