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Synthesis 2017; 49(19): 4414-4433
DOI: 10.1055/s-0036-1589094
short review
© Georg Thieme Verlag Stuttgart · New York

Reactions of Arynes Involving Transition-Metal Catalysis

Minghao Feng
a   Shanghai Key Laboratory of Green Chemistry and Chemical Process, School of Chemistry and Molecular Engineering, East China Normal University, 3663 North Zhongshan Road, Shanghai, 200062, P. R. of China   Email: xfjiang@chem.ecnu.edu.cn
,
Xuefeng Jiang  *
a   Shanghai Key Laboratory of Green Chemistry and Chemical Process, School of Chemistry and Molecular Engineering, East China Normal University, 3663 North Zhongshan Road, Shanghai, 200062, P. R. of China   Email: xfjiang@chem.ecnu.edu.cn
b   State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin, P. R. of China
c   State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China
› Author AffiliationsWe are grateful for financial support provided by NSFC (21672069, 21472050), DFMEC (20130076110023), Fok Ying Tung Education Foundation (141011), Program for Shanghai Rising Star (15QA1401800), Professor of Special Appointment (Eastern Scholar) at Shanghai Institutions of Higher Learning, and the National Program for Support of Top-notch Young Professionals.

Further Information

Publication History

Received: 09 May 2017

Accepted after revision: 12 July 2017

Publication Date:
22 August 2017 (online)

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Abstract

Arynes are important building blocks for introducing aromatic rings into molecules and they are frequently utilized in syntheses. Historically, arynes were generated under harsh conditions and this limited their use. Arynes can now be generated under milder conditions, e.g. from 2-(trimethylsilyl)phenyl triflate, and utilized in transition-metal­ catalyzed reactions such as [2+2+2] reactions, insertion into σ-bonds, cascade cyclizations and C–H activation reactions. This short review focuses on transition-metal-catalyzed reactions relevant to aryne intermediates generated from 2-(trimethylsilyl)phenyl triflates and other aryne precursors.

1 Introduction

2 [2+2+2] Reactions

3 Aryne Insertion into a σ-Bond

4 Cascade Cyclizations

5 C–H Activation

6 Multicomponent Reactions (MCRs)

7 Conclusion

Key words

aryne - transition-metal catalysis - aromatic ring - multi­component reactions - C–H activation
 

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