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Synthesis 2022; 54(19): 4329-4338
DOI: 10.1055/a-1866-7737
paper

Palladium/Norbornene-Cocatalyzed Three-Component Synthesis of ortho-Acylated Benzonitriles

Liqin Wang‡
a   Engineering Research Center of Pharmaceutical Process Chemistry, Ministry of Education, Shanghai Key Laboratory of New Drug Design, School of Pharmacy, and State Key Laboratory of Bioengineering Reactors, East China University of Science & Technology, 130 Meilong Road, Shanghai 200237, P. R. of China
,
Guangjun Song‡
a   Engineering Research Center of Pharmaceutical Process Chemistry, Ministry of Education, Shanghai Key Laboratory of New Drug Design, School of Pharmacy, and State Key Laboratory of Bioengineering Reactors, East China University of Science & Technology, 130 Meilong Road, Shanghai 200237, P. R. of China
,
Qiufang Wu
a   Engineering Research Center of Pharmaceutical Process Chemistry, Ministry of Education, Shanghai Key Laboratory of New Drug Design, School of Pharmacy, and State Key Laboratory of Bioengineering Reactors, East China University of Science & Technology, 130 Meilong Road, Shanghai 200237, P. R. of China
,
Jiaxin Qin
a   Engineering Research Center of Pharmaceutical Process Chemistry, Ministry of Education, Shanghai Key Laboratory of New Drug Design, School of Pharmacy, and State Key Laboratory of Bioengineering Reactors, East China University of Science & Technology, 130 Meilong Road, Shanghai 200237, P. R. of China
,
Xinhong Yu  ∗
a   Engineering Research Center of Pharmaceutical Process Chemistry, Ministry of Education, Shanghai Key Laboratory of New Drug Design, School of Pharmacy, and State Key Laboratory of Bioengineering Reactors, East China University of Science & Technology, 130 Meilong Road, Shanghai 200237, P. R. of China
,
Niangen Chen∗
b   School of Pharmacy, Hainan Medical University, Haikou 571199, P. R. of China
,
Cuiqing Li∗
c   College of Chemical Engineering, Beijing Institute of Petrochemical Technology, 19 North Qingyuan Road, Daxing District, Beijing 102617
› InstitutsangabenWe gratefully acknowledge financial support from the National Natural Science Foundation of China (21476078) and the Science and Technology Commission of Shanghai Municipality (12431900902).
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Abstract

A palladium/norbornene-cocatalyzed Catellani-type ortho-C–H-acylation/ipso-cyanation of iodoarenes is developed via a three-component approach using safe and low-toxic sodium carboxylates as the acyl sources and CuCN as the CN source, affording the desired products in yields of 50–94%. Without introducing a directing group on the substrate, a catalytic amount of norbornene and palladium can regioselectively activate the ortho-C–H bonds of iodoarenes. The reaction exhibits good functional group tolerance and works well on gram-scale. In addition, this transformation allows rapid and convenient access toward isoindolinones, 1,4-dicarbonyl compounds and ortho-aminated benzonitriles by manipulation of the cyano and carbonyl groups.

Key words

palladium - C–H activation - acylation - arenes - synthetic methods

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1866-7737.
  • Supporting Information


Publikationsverlauf

Eingereicht: 31. März 2022

Angenommen nach Revision: 01. Juni 2022

Accepted Manuscript online:
01. Juni 2022

Artikel online veröffentlicht:
05. Juli 2022

© 2022. Thieme. All rights reserved

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