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Synthesis 2022; 54(18): 3928-3940
DOI: 10.1055/s-0041-1737493
DOI: 10.1055/s-0041-1737493
short review
Recent Advances in Thianthrenation/Phenoxathiination Enabled Site-Selective Functionalization of Arenes
We gratefully acknowledge National Natural Science Foundation of China (22101291, 22171277, 21821002), Shanghai Rising-Star Program (20QA1411400), Shanghai Institute of Organic Chemistry, and State Key Laboratory of Organometallic Chemistry for financial support.
Abstract
Site-selective functionalization of simple arenes remains a paramount challenge due to the similarity of multiple C–H bonds in the same molecule with similar steric environment and electronic properties. Recently, the site-selective thianthrenation/phenoxathiination of arenes has become an attractive solution to reach this challenging goal and it has been applied in the late-stage functionalization of various bioactive molecules. This short review aims to summarize recent advances in the site-selective C–H functionalization of arenes via aryl thianthrenium salts, as well as mechanistic insights in the remarkable site-selectivity obtained in thianthrenation step.
1 Introduction
2 Site-Selective Thianthrenation of Arenes and Mechanistic Insight
3 Thianthrenation-Enabled Site-Selective Functionalization of Arenes
3.1 Thianthrenation-Enabled C(sp 2)–C Bond Formation Reaction
3.2 Thianthrenation-Enabled C(sp 2)–X Bond Formation Reaction
4 Conclusion and Outlook
Publication History
Received: 08 April 2022
Accepted after revision: 02 May 2022
Article published online:
28 June 2022
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For selected reviews on non-directed C–H activation:
For selected reviews on late-stage functionalization:
For selected reviews on directing group approaches for meta- and para-functionalization, see:
For selected reviews on sulfonium salts:
For selected examples on other sulfonium salts mediated C–H functionalization: