Transfer of Sulfur: From Simple to Diverse

Abstract

The introduction of sulfur atoms onto target molecules is an important area in organic synthesis, in particular in the synthesis of pharmaceutical compounds, and a wide variety of sulfuration agents have been developed for thionation reactions over the past few decades. In this Focus Review, we collect and summarize the C-S bond-formation reactions that have been used to construct C-S bonds in natural products and pharmaceutical compounds.

One‐Pot Copper‐Catalysed Thioetherification of Aryl Halides Using Alcohols and Lawesson's Reagent in Diglyme

“…Subsequently, these odourless methods were developed using other sulfur surrogates [9] such as xanthogenate, [10] thioacetamide, [11] thiourea, [12] potassium thiocyanate, [13] thioacetate, [14] sodium hydrosulfide, [15] sodium sulfide, [16] elemental sulfur, [17] sulfonyl hydrazides, [18] Na 2 S 2 O 3 , [19] potassium 5-methyl-1,3,4-oxadiazole-2-thiolate, [20] aminothiourea, [21] sulfonyl hydrazide, [22] and phosphorothioic acids and related compounds. [23] However, the challenge of designing new synthetic and catalytic systems for C-S bond formation under mild and greener reaction conditions remains.…”

Synthesis of Air‐stable, Odorless Thiophenol Surrogates via Ni‐Catalyzed C−S Cross‐Coupling

“…[a] [a] Yields are of isolatedm aterial from reactionsp erformed on a1mmol scale;v aluesi np arenthesis refer to yieldso fi sothiouronium iodides determined by NMRs pectroscopica nalysis prior to isolation. Thes ubstrate scope extends to synthetically versatile substituents that would not necessarily be tolerated by the basic/nucleophilic conditions of conventional Migita coupling (30-39), [2] most notably at erminal alkyne (34), Michael acceptors (35 and 36) [19] and the fluorenylmethyloxycarbonyl (Fmoc) protecting group (37). [18] Ab road range of functionalities are well-tolerated, including unprotected anilines,p henolsa nd alcohols (25)(26)(27).…”

Catalytic Formation of Silicon–Heteroatom (N, P, O, S) Bonds

“…Organosulfur chemistry is a very challenging area of chemistry in general, and in particular, catalytic methods to form sulfur species garner high interest because of the notorious examples of catalyst poisoning by sulfur compounds. Recently, chemists have tried to obtain thiosilanes by various transformations that are mainly based on the dehydrocoupling reaction.…”