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

Yıl 2020, Cilt: 8 Sayı: 1, 22 - 27, 30.06.2020

Nevroz Aslan Ertaş Arif Kıvrak

Öz

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.

Anahtar Kelimeler

ferrocene, naphthoquinone, rearrangement reactions

Destekleyen Kurum

TUBITAK

Proje Numarası

114Z042

Teşekkür

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.

Kaynakça

• [1] R. B. Semwal, D. K. Semwal, S. Combrinck, C. Cartwright-Jones, A. Viljoen, Journal of Ethnopharmacology 2014, 155, 80-103; L. Zhou, X. Zhang, W. Zhou, Chemistry Central Journal 2017, 11; A. Denis, P. Palvadeau, P. Molinie, O. Chauvet, K. Boubekeur, Solid State Sciences 2001, 3, 715-725.
• [2] R. A. Sharma, B. Singh, D. Singh, P. Chandrawat, Journal of Medicinal Plants Research 2009, 3, 1153-1175; B. B. Carbas, A. Kivrak, M. Zora, A. M. Onal, Reactive & Functional Polymers 2011, 71, 579-587; R. M. Cory, D. M. McKnight, Environmental Science & Technology 2005, 39, 8142-8149.
• [3] B. N. Poul, J. R. Vakil, Asian Journal of Chemistry 1998, 10, 639-640.
• [4] G. Abbas, Z. Hassan, A. Al-Harrasi, A. Khan, A. Al-Adawi, M. Ali, Journal of Molecular Structure 2019, 1195, 462-469.
• [5] I. Kim, G. Chhetri, J. Kim, T. Seo, Antonie Van Leeuwenhoek International Journal of General and Molecular Microbiology 2019, 112, 1731-1738.
• [6] G. A. M. Jardim, E. H. G. da Cruz, W. O. Valenca, D. J. B. Lima, B. C. Cavalcanti, C. Pessoa, J. Rafique, A. L. Braga, C. Jacob, E. N. da Silva, Molecules 2018, 23.
• [7] M. Michalik, P. Poliak, V. Lukes, E. Klein, Phytochemistry 2019, 166.
• [8] M. M. Zangeneh, A. Zangeneh, Applied Organometallic Chemistry.
• [9] N. Yu, X. Li, M. Wen, P. Geng, X. L. Ren, Z. J. Wang, Z. G. Chen, Journal of Nanoscience and Nanotechnology 2020, 20, 2032-2039.
• [10] O. Moaven, K. I. Votanopoulos, P. Shen, P. Mansfield, D. L. Bartlett, G. Russell, R. McQuellon, J. H. Stewart, E. A. Levine, Annals of Surgical Oncology.
• [11] T. Ishikawa, Pharmacogenomics 2012, 13, 633-636.
• [12] W. Y. Huang, Y. Z. Cai, Y. B. Zhang, Nutrition and Cancer-an International Journal 2010, 62, 1-20; L. F. Tietze, H. P. Bell, S. Chandrasekhar, Angewandte Chemie-International Edition 2003, 42, 3996-4028.
• [13] G. D. Fang, J. Gao, D. D. Dionysiou, C. Liu, D. M. Zhou, Environmental Science & Technology 2013, 47, 4605-4611.
• [14] M. Zora, A. Kivrak, Y. Kelgokmen, Journal of Organometallic Chemistry 2014, 759, 67-73.
• [15] M. M. Santos, P. Bastos, I. Catela, K. Zalewska, L. C. Branco, Mini-Reviews in Medicinal Chemistry 2017, 17, 771-784.
• [16] A. Kivrak, C. Zobi, Y. Torlak, Y. Camlisoy, M. Kus, H. Kivrak, Applied Organometallic Chemistry 2018, 32. N. Aslan-Ertas, E. Kavak, F. Salma, H. Celik-Kazici, H. Kivrak, A. Kivrak, Electroanalysis 2020, just accepted.
• [17] X. Y. Wang, Q. Li, J. J. Xu, S. Wu, T. F. Xiao, J. Hao, P. Yu, L. Q. Mao, Analytical Chemistry 2016, 88, 5885-5891.
• [18] L. Guyon, E. Lepeltier, J. C. Gimel, B. Calvignac, F. Franconi, N. Lautram, A. Dupont, C. Bourgaux, P. Pigeon, P. Saulnier, G. Jaouen, C. Passirani, Journal of Physical Chemistry Letters 2019, 10, 6613-6620.
• [19] A. Kivrak, M. Zora, Journal of Organometallic Chemistry 2007, 692, 2346-2349; M. Zora, A. Kivrak, C. Yazici, Journal of Organic Chemistry 2011, 76, 6726-6742.
• [20] B. Yucel, B. Sanli, H. Soylemez, I. Yilmaz, Tetrahedron 2011, 67, 1406-1421.
• [21] B. B. Carbas, A. Kivrak, E. Kayak, Materials Chemistry and Physics 2017, 188, 68-74.
• [22] O. Sahin, H. Kivrak, A. Kivrak, H. C. Kazici, O. Alal, D. Atbas, International Journal of Electrochemical Science 2017, 12, 762-769; M. Guler, V. Turkoglu, A. Kivrak, F. Karahan, Materials Science & Engineering C-Materials for Biological Applications 2018, 90, 454-460.
• [23] Z. Hassan, I. Ullah, I. Ali, R. A. Khera, I. Knepper, A. Ali, T. Patonay, A. Villinger, P. Langer, Tetrahedron 2013, 69, 460-469.
• [24] C. H. Cho, D. I. Jung, B. Neuenswander, R. C. Larock, Acs Combinatorial Science 2011, 13, 501-510.
• [25] S. Kotha, A. K. Ghosh, Synlett 2002, 451-452; M. A. S. Algso, A. Kivrak, Chemical Papers 2019, 73, 977-985.
• [26] S. Yoshida, H. Kubo, T. Saika, S. Katsumura, Chemistry Letters 1996, 139-140.
• [27] W. M. Best, C. G. Sims, M. Winslade, Australian Journal of Chemistry 2001, 54, 401-404.
• [28] M. W. Davies, C. N. Johnson, J. P. A. Harrity, Journal of Organic Chemistry 2001, 66, 3525-3532.
• [29] R. P. Hsung, Y. C. Xu, W. D. Wulff, Tetrahedron Letters 1995, 36, 8159-8162.
• [30] P. Patil, A. Nimonkar, K. G. Akamanchi, Journal of Organic Chemistry 2014, 79, 2331-2336.
• [31] Y. Fujiwara, V. Domingo, I. B. Seiple, R. Gianatassio, M. Del Bel, P. S. Baran, Journal of the American Chemical Society 2011, 133, 3292-3295.
• [32] J. Wang, S. Wang, G. Wang, J. Zhang, X. Q. Yu, Chemical Communications 2012, 48, 11769-11771.
• [33] K. Komeyama, T. Kashihara, K. Takaki, Tetrahedron Letters 2013, 54, 1084-1086.
• [34] Y. J. Wang, S. Zhu, L. H. Zou, European Journal of Organic Chemistry 2019, 2019, 2179-2201; P. P. Singh, S. K. Aithagani, M. Yadav, V. P. Singh, R. A. Vishwakarma, Journal of Organic Chemistry 2013, 78, 2639-2648; P. Ashok, A. Ilangovan, Tetrahedron Letters 2018, 59, 438-441.
• [35] A. Ilangovan, A. Polu, G. Satish, Organic Chemistry Frontiers 2015, 2, 1616-1620.