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

Year 2020, Volume: 8 Issue: 1, 22 - 27, 30.06.2020

Nevroz Aslan Ertaş , Arif Kıvrak

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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