When Aryne Chemistry Meets Organosulfur Compounds

Dedicated to Professor Hisashi Yamamoto on the occasion of his 80th birthday.

Abstract

Organosulfur compounds are ubiquitous in agrochemicals, active pharmaceutical ingredients, natural products, catalysts, and functional materials. The efficient assembly of sulfur-containing skeletons through S(IV) intermediates has emerged as an actively explored direction in organic synthesis. In the past 7 years, our research group has been devoted to developing aryne-induced, sulfonium-zwitterion-based synthetic methodologies. In this account, we systematically overview our recent efforts on this topic, including sigmatropic rearrangements, ring opening of cyclic sulfides, and selective S-arylation of thio-oxindoles. These distinct protocols feature mild conditions and avoid the use of transition metals, allowing facile access to structurally diverse organosulfur compounds. The working hypothesis for our reaction design and key historical precedents are also critically discussed. Our goal is to achieve selectivity control and diversity-oriented synthesis, further advancing sulfonium zwitterion chemistry in the direction of precision synthesis.

1 Introduction

2 Sigmatropic Rearrangement

3 Ring Opening of Cyclic Sulfides

4 Selective Arylation of Thio-oxindoles

5 Conclusion

Key words

aryne - zwitterion - sulfonium salt - sulfur ylide - organosulfur compound - precision chemistry

Publication History

Received: 29 May 2023

Accepted after revision: 15 June 2023

Article published online:
12 July 2023

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