Sulfonyl Hydrazides in Organic Synthesis: A Review of Recent Studies

Sulfonyl hydrazides are widely used as organic reagents. Advances in the past decade are summarized in the following categories by key intermediates: (1) [RO2S center dot]; (2) RO2SSR; (3) [ArS center dot]; (4) [RO2S-]; (5) RSO2-[Metal] species; (6) Ar-[Metal] species; (7) RSX; (8) RS-DBU; (9) nucleophilic amino group; (10) sulfonyl hydrazides as diazene or sulfinic acid surrogate. Reactions with alkenes, alkynes, aldehydes, alcohols, thiophenol, Grignard reagents, among others, are discussed. We hope this review will promote future research in this area. 1. Introduction 2. Sulfonyl Radiacls-Mediated Reactions 2.1. Addition to Unsaturated Bonds 2.2. C-H Activation 2.3. C-S Coupling 2.4. N-S Coupling 2.5. O-S Coupling 2.6. F-S Coupling 3. Formation and Application of Thiosulfonates 3.1. Formation of Thiosulfonates 3.2. Application of in situ Generated Thiosulfonate 4. ArS Radical-Mediated Reaction 5. Sulfur-Centered Anions 6. RSO2-[Metal] Intermediates 7. Electrophilic RX Intermediates 8. Electrophilic RS-DBU Intermediates 9. Ar-[Metal] Intermediates 10. Nucleophilic Sulfonyl Hydrazides 11. As Diazene or Sulfinic Acid Surrogate 12. Conclusions