Synthesis 2016; 48(14): 2137-2150
DOI: 10.1055/s-0035-1561641
short review
© Georg Thieme Verlag Stuttgart · New York

Bridging Fluorine and Aryne Chemistry: Vicinal Difunctionalization of Arynes Involving Nucleophilic Fluorination, Trifluoromethylation, or Trifluoromethylthiolation

Yuwen Zeng
Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Ling-Ling Road, Shanghai 200032, P. R. of China   Email: jinbohu@sioc.ac.cn
,
Jinbo Hu*
Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Ling-Ling Road, Shanghai 200032, P. R. of China   Email: jinbohu@sioc.ac.cn
› Author Affiliations
Further Information

Publication History

Received: 31 January 2016

Accepted after revision: 18 April 2016

Publication Date:
24 May 2016 (eFirst)

Abstract

Multi-functionalized fluorinated arenes, especially those that are transformable fluorinated building blocks, are intriguing compounds in synthetic chemistry and for life science related applications. The development of straightforward and efficient approaches to these compounds is of significant importance and has, therefore, attracted much attention. This short review presents our recent progress on the fluoro-difunctionalization of arynes, which allows facile construction of a series of fluorinated arene building blocks bearing an ortho-iodine substituent as a coupling handle for further elaboration.

1 Introduction

2 Silver-Mediated Trifluoromethylation–Iodination of Arynes

3 Silver-Catalyzed Insertion of Aryne into Rf–I Bonds

4 Diphenyliodonium-Catalyzed Fluorination of Arynes

5 Silver-Mediated Trifluoromethylthiolation–Iodination of Arynes

6 Summary and Outlook

 
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