Ru-Catalyzed C(sp2)−H Bond Arylation of Benzamides Bearing a Novel 4-Aminoantipyrine as a Directing Group

Hamad H. Al Mamari; Diana Al Kiumi; Tamadher Al Rashdi; Huda Al Quraini; Malak Al Rashdi; Sumayya Al Sheraiqi; Sara Al Harmali; Mohammed Al Lamki; Ahmed Al Sheidi; Asma Al Zadjali

doi:10.1002/ejoc.202100513

Ru-Catalyzed C(sp²)−H Bond Arylation of Benzamides Bearing a Novel 4-Aminoantipyrine as a Directing Group

Hamad H. Al Mamari^*, Diana Al Kiumi, Tamadher Al Rashdi, Huda Al Quraini, Malak Al Rashdi, Sumayya Al Sheraiqi, Sara Al Harmali, Mohammed Al Lamki, Ahmed Al Sheidi, Asma Al Zadjali

^*Corresponding author for this work

Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

A novel design-based removable N,O-bidentate directing group based on cheap and commercially available 4-aminoantipyrine (AAP) is reported. Aromatic AP amides bearing 4-aminoantipyrine underwent efficient Ru-catalyzed C(sp²)−H arylation using [RuCl₂(PPh₃)₃] as a catalyst and aryl bromides as electrophiles. The novel bidentate directing group enabled the C−H functionalization reaction with good scope, good functional group tolerance and in decent yields.

Original language	English
Pages (from-to)	3598-3603
Number of pages	6
Journal	European Journal of Organic Chemistry
Volume	2021
Issue number	25
DOIs	https://doi.org/10.1002/ejoc.202100513
Publication status	Published - Jul 7 2021

Keywords

4-Aminoantipyrine
Chelation Assistance
C−H Functionalization
Directing group
Ru-Catalysis

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1002/ejoc.202100513

Cite this

Al Mamari, H. H., Al Kiumi, D., Al Rashdi, T., Al Quraini, H., Al Rashdi, M., Al Sheraiqi, S., Al Harmali, S., Al Lamki, M., Al Sheidi, A., & Al Zadjali, A. (2021). Ru-Catalyzed C(sp²)−H Bond Arylation of Benzamides Bearing a Novel 4-Aminoantipyrine as a Directing Group. European Journal of Organic Chemistry, 2021(25), 3598-3603. https://doi.org/10.1002/ejoc.202100513

Al Mamari, HH, Al Kiumi, D, Al Rashdi, T, Al Quraini, H, Al Rashdi, M, Al Sheraiqi, S, Al Harmali, S, Al Lamki, M, Al Sheidi, A & Al Zadjali, A 2021, 'Ru-Catalyzed C(sp²)−H Bond Arylation of Benzamides Bearing a Novel 4-Aminoantipyrine as a Directing Group', European Journal of Organic Chemistry, vol. 2021, no. 25, pp. 3598-3603. https://doi.org/10.1002/ejoc.202100513

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abstract = "A novel design-based removable N,O-bidentate directing group based on cheap and commercially available 4-aminoantipyrine (AAP) is reported. Aromatic AP amides bearing 4-aminoantipyrine underwent efficient Ru-catalyzed C(sp2)−H arylation using [RuCl2(PPh3)3] as a catalyst and aryl bromides as electrophiles. The novel bidentate directing group enabled the C−H functionalization reaction with good scope, good functional group tolerance and in decent yields.",

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AU - Al Rashdi, Tamadher

AU - Al Quraini, Huda

AU - Al Rashdi, Malak

AU - Al Sheraiqi, Sumayya

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AU - Al Zadjali, Asma

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