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Synlett 2021; 32(02): 142-158
DOI: 10.1055/s-0040-1707217
cluster
© Georg Thieme Verlag Stuttgart · New York

Recent Advances in Sulfur-Containing Heterocycle Formation via Direct C–H Sulfuration with Elemental Sulfur

Saiwen Liu
a   College of Materials and Chemical Engineering, Hunan City University, Yiyang 413000, P. R. of China
b   Key Laboratory for Green Organic Synthesis and Application of Hunan Province, Key Laboratory of Environmentally Friendly Chemistry and Application of Ministry of Education, College of Chemistry, Xiangtan University, Xiangtan 411105, P. R. of China   Email: gjdeng@xtu.edu.cn   Email: hwhuang@xtu.edu.cn
,
Guo-Jun Deng∗
b   Key Laboratory for Green Organic Synthesis and Application of Hunan Province, Key Laboratory of Environmentally Friendly Chemistry and Application of Ministry of Education, College of Chemistry, Xiangtan University, Xiangtan 411105, P. R. of China   Email: gjdeng@xtu.edu.cn   Email: hwhuang@xtu.edu.cn
,
Huawen Huang∗
b   Key Laboratory for Green Organic Synthesis and Application of Hunan Province, Key Laboratory of Environmentally Friendly Chemistry and Application of Ministry of Education, College of Chemistry, Xiangtan University, Xiangtan 411105, P. R. of China   Email: gjdeng@xtu.edu.cn   Email: hwhuang@xtu.edu.cn
› Author AffiliationsWe thank the Normal Project Foundation of Hunan Provincial Education Department (18C0845), the National Natural Science Foundation of China (21871226), and the Science and Technology Planning Project of Hunan Province (2019RS2039) for financial support.
Further Information

Publication History

Received: 29 May 2020

Accepted after revision: 30 June 2020

Publication Date:
07 August 2020 (online)

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Published as part of the Cluster Modern Heterocycle Synthesis and Functionalization

Abstract

The synthesis of sulfur heterocycles via the construction of C–S bonds has received considerable attention due to their biological value and extensive pharmaceutical application. While diverse sulfurating agents have been developed over the past few decades, in this regard, elemental sulfur, with advantages of low toxicity, odorless nature and chemical stability, has great potential for the construction of diverse sulfur heterocycles through its direct incorporation into the target molecules in a concise way. Direct functionalization of inert C–H bonds can shorten the number of reaction steps and minimize the amount of waste formed. Hence, heteroannulations via direct C–H sulfuration is considered to be an attractive strategy for the synthesis of sulfur heterocycles. In the last few years, a vast array of concise systems have been reported for the synthesis of some valuable sulfur heterocycles such as thiophenes, thienoindoles, thienothiazoles, thiazoles, benzothiazoles, and thiadiazoles through direct C–H sulfuration/annulations with elemental sulfur. These are discussed in detail in this review.

1 Introduction

2 Thiophenes

3 Thienoindoles

4 Thienothiazoles

5 Other Fused Thiophenes

6 Thiazoles

7 Benzothiazoles

8 Thiadiazoles

9 Others

10 Summary and Outlook

Key words

sulfur heterocycles - C–H sulfuration - elemental sulfur - concise synthesis - multicomponent reactions