Synlett 2019; 30(02): 129-140
DOI: 10.1055/s-0037-1611057
account
© Georg Thieme Verlag Stuttgart · New York

Development of New Electrophiles in Palladium/Norbornene-Catalyzed ortho-Functionalization of Aryl Halides

Kun Zhao
,
Linlin Ding
,
Zhenhua Gu*
This work was partly supported by NSFC (21622206, 21472179), and the Fundamental Research Funds for the Central Universities (WK2060190086).
Further Information

Publication History

Received: 09 August 2018

Accepted after revision: 05 September 2018

Publication Date:
02 October 2018 (online)


Abstract

This account focuses on our work in palladium/norbornene-catalyzed selective ortho-arylation and ortho-acylation of aryl halides. It will discuss our synthetic plan, initial design and revised strategy in the enantioselective synthesis of the rhazinal family of natural products. It also shows our efforts on the α-acylation reaction by the cleavage of various C(O)–X bonds, along with some mechanistic studies.

1 Introduction

2 Synthesis of the Rhazinal Family of Natural Products

2.1 Initial Design

2.2 Revised Strategy

2.3 Enantioselective Synthesis of the Rhazinal Family of Natural Products

3 Catalytic ortho-Acylation

3.1 Acid Chloride and Anhydride Strategy

3.2 Cleavage of C(O)–S Bond of Thioesters by Pd, Norbornene and Copper Cocatalysis

4 Decarboxylative Alkynylation

5 Conclusion

 
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