Research Article

Ferrocene as a leaving group; Unexpected rearrangement reactions for the synthesis of 2,3-diarylnapthoquinones

Volume: 8 Number: 1 June 30, 2020
EN

Ferrocene as a leaving group; Unexpected rearrangement reactions for the synthesis of 2,3-diarylnapthoquinones

Abstract

In general, Suzuki-Miyaura coupling reaction between aryl bromide and arylboronic acids form the new C-C bond in the presence of Pd-catalyst. In the present study, 2-bromo-3-ferrocenyl-1,4-naphthoquinone 2 intermediate is synthesized by starting from 2,3-dibromo-1,4-naphthoquinone via Suzuki-Miyaura Coupling reaction. Then, it is investigated that the reaction between 2 and arylboronic acids give a new rearrangement reaction involving free radicals. Ferrocene structure displays critical roles for the formation of 2,3-diaryl-1,4-naphthoquinones. This reaction could be first example for the radical C-C bond cleavage reactions including ferrocene.

Keywords

ferrocene,naphthoquinone,rearrangement reactions

Supporting Institution

TUBITAK

Project Number

114Z042

Thanks

We want to express our thanks to the Scientific and Technical Research Council of Turkey (TUBİTAK-114Z042) for financial supports of Microwave Reactor and Van Yüzüncü Yil University (FBA-2019-7910) for financial supports of chemicals. N. A. also thanks to YÖK 100/2000 for scholarships.

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APA
Aslan Ertaş, N., & Kıvrak, A. (2020). Ferrocene as a leaving group; Unexpected rearrangement reactions for the synthesis of 2,3-diarylnapthoquinones. MANAS Journal of Engineering, 8(1), 22-27. https://izlik.org/JA35CN29WJ
AMA
1.Aslan Ertaş N, Kıvrak A. Ferrocene as a leaving group; Unexpected rearrangement reactions for the synthesis of 2,3-diarylnapthoquinones. MJEN. 2020;8(1):22-27. https://izlik.org/JA35CN29WJ
Chicago
Aslan Ertaş, Nevroz, and Arif Kıvrak. 2020. “Ferrocene As a Leaving Group; Unexpected Rearrangement Reactions for the Synthesis of 2,3-Diarylnapthoquinones”. MANAS Journal of Engineering 8 (1): 22-27. https://izlik.org/JA35CN29WJ.
EndNote
Aslan Ertaş N, Kıvrak A (June 1, 2020) Ferrocene as a leaving group; Unexpected rearrangement reactions for the synthesis of 2,3-diarylnapthoquinones. MANAS Journal of Engineering 8 1 22–27.
IEEE
[1]N. Aslan Ertaş and A. Kıvrak, “Ferrocene as a leaving group; Unexpected rearrangement reactions for the synthesis of 2,3-diarylnapthoquinones”, MJEN, vol. 8, no. 1, pp. 22–27, June 2020, [Online]. Available: https://izlik.org/JA35CN29WJ
ISNAD
Aslan Ertaş, Nevroz - Kıvrak, Arif. “Ferrocene As a Leaving Group; Unexpected Rearrangement Reactions for the Synthesis of 2,3-Diarylnapthoquinones”. MANAS Journal of Engineering 8/1 (June 1, 2020): 22-27. https://izlik.org/JA35CN29WJ.
JAMA
1.Aslan Ertaş N, Kıvrak A. Ferrocene as a leaving group; Unexpected rearrangement reactions for the synthesis of 2,3-diarylnapthoquinones. MJEN. 2020;8:22–27.
MLA
Aslan Ertaş, Nevroz, and Arif Kıvrak. “Ferrocene As a Leaving Group; Unexpected Rearrangement Reactions for the Synthesis of 2,3-Diarylnapthoquinones”. MANAS Journal of Engineering, vol. 8, no. 1, June 2020, pp. 22-27, https://izlik.org/JA35CN29WJ.
Vancouver
1.Nevroz Aslan Ertaş, Arif Kıvrak. Ferrocene as a leaving group; Unexpected rearrangement reactions for the synthesis of 2,3-diarylnapthoquinones. MJEN [Internet]. 2020 Jun. 1;8(1):22-7. Available from: https://izlik.org/JA35CN29WJ