Bond-Forming and -Breaking Reactions at Sulfur(IV): Sulfoxides, Sulfonium Salts, Sulfur Ylides, and Sulfinate Salts

• Published in: Chemical reviews Vol. 119; no. 14; pp. 8701 - 8780
• Main Authors: Kaiser, Daniel, Klose, Immo, Oost, Rik, Neuhaus, James, Maulide, Nuno
• Format: Journal Article
• Language: English
• Published: United States American Chemical Society 24.07.2019
• Subjects: chemical structure; Chemistry; cleavage (chemistry); Organic chemistry; organic sulfur compounds; Organosulfur compounds; Review; salts; Sulfonium salts; Sulfur
• ISSN: 0009-2665; 1520-6890; 1520-6890
• DOI: 10.1021/acs.chemrev.9b00111

Organosulfur compounds have long played a vital role in organic chemistry and in the development of novel chemical structures and architectures. Prominent among these organosulfur compounds are those involving a sulfur­(IV) center, which have been the subject of countless investigations over more than a hundred years. In addition to a long list of textbook sulfur-based reactions, there has been a sustained interest in the chemistry of organosulfur­(IV) compounds in recent years. Of particular interest within organosulfur chemistry is the ease with which the synthetic chemist can effect a wide range of transformations through either bond formation or bond cleavage at sulfur. This review aims to cover the developments of the past decade in the chemistry of organic sulfur­(IV) molecules and provide insight into both the wide range of reactions which critically rely on this versatile element and the diverse scaffolds that can thereby be synthesized.