Abstract

The construction of a C-S bond is a powerful strategy for the synthesis of sulfur containing compounds including sulfides, sulfoxides, and sulfones. Recent methodological developments have revealed lots of novel protocols for C-S bond formation, providing easy access to sulfur containing compounds. Unlike traditional Ullmann typed C-S coupling reaction, the recently developed reactions frequently use non-halide compounds, such as diazo compounds and simple arenes/alkanes instead of aryl halides as substrates. On the other hand, novel C-S coupling reaction pathways involving thiyl radicals have emerged as an important strategy to construct C-S bonds. In this review, we focus on the recent advances on the synthesis of sulfides, sulfoxides, and sulfones from non-halide substrates involving C-S bond construction.

Highlights

  • Sulfur containing compounds are a fundamental building block in organic synthesis [1,2].They are of great significance in bioactive natural products, pharmaceutical drugs, pesticides, and materials [3,4,5,6,7,8]

  • The traditional Ullmann typed reaction, which has been well established in the past several decades, has provided lots of synthetic protocols for diaryl sulfides and aryl alkyl sulfides through transition-metal catalyzed C-S coupling reaction of aryl halides with aryl thiols or other sulfur precursors [9,10,11]

  • The research on the synthetic methods for organosulfur compounds is of great importance in both academic research and industry

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Summary

Introduction

Sulfur containing compounds are a fundamental building block in organic synthesis [1,2]. They are of great significance in bioactive natural products, pharmaceutical drugs, pesticides, and materials [3,4,5,6,7,8]. Sulfur containing compounds, such as sulfides, sulfoxides, and sulfones, constitute a large portion of pharmaceutical drugs possessing a variety of biological activities. The construction of C-S bond is considered as an efficient strategy for the synthesis of sulfur containing compounds. We highlight the very recent advances in novel strategies that take advantage of C-S bond construction for the synthesis of sulfides, sulfoxides, and sulfones from non-halide substrates.

Synthesis of Sulfides via C-S Bond Construction
Disulfide as Sulfenylation Source
Thiol as Sulfenylation Source
Elemental Sulfur as Sulfenylation Source
Sulfonyl Derivative as the Sulfenylation Source
Other Sulfenylation Sources
Trifluoromethylthio Reagents as Sulfenylation Sources
Synthesis of Sulfoxides via C-S Bond Construction
Synthesis of Sulfones via C-S Bond Construction
Findings
Conclusions and Prospects
Full Text
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