An Efficient Palladium-Thiourea Catalysed Heck Cross-Coupling Reaction for Molecular Electronic Interest

Authors

Wan M. Khairul, School of Fundamental Science, Universiti Malaysia Terengganu, 21030 Kuala Terengganu, Terengganu, MalaysiaFollow
Mohd Shahrul Shahmi Md Shariff, School of Fundamental Science, Universiti Malaysia Terengganu, 21030 Kuala Terengganu, Terengganu, Malaysia
Rafizah Rahamathullah, School of Fundamental Science, Universiti Malaysia Terengganu, 21030 Kuala Terengganu, Terengganu, Malaysia
Adibah Izzati Daud, School of Fundamental Science, Universiti Malaysia Terengganu, 21030 Kuala Terengganu, Terengganu, Malaysia
Mustaffa Shamsuddin, Department of Chemistry, Faculty of Science, Universiti Teknologi Malaysia, 81310 Skudai, Johor, Malaysia
Siti Kamilah Che Soh, School of Marine Science and Environment, Universiti Malaysia Terengganu, 21030 Kuala Terengganu, Terengganu, Malaysia

Abstract

The synthesis and utilization of C-C bonds formation are concerned about the key steps for the building of several conducting molecular electronics involving many asymmetric catalysts approached, which is an essential task that most researchers would ignore in preparing these materials to enhance the production yield of cross-coupling materials. Despite the enormous progress, there still remains a great demand for economic and practicable cross-coupling processes involving ultra-low catalyst loadings with high turnover numbers due to the employment of conventional metal catalyst. Thus, there has been an excessive interest to cultivate non-phosphine palladium catalysts for excellent achievement of activity, stability, and substrate tolerance which permit the coupling reactions to be conducted under mild reaction condition at ambient atmosphere. In this contribution, N-(4-nitrophenylcarbamothioyl)-N’-(4- methylbenzoyl) thiourea (LT1) and its metal complex of MLT1 featuring Pd (II) have been successfully characterised via typical spectroscopic methods namely; Infrared (IR) spectroscopy, Ultraviolet-visible (UV-Vis) spectroscopy, CHNS elemental analysis, and Nuclear Magnetic Resonance (1H and 13C NMR). In turn, catalytic studies of palladium catalyst (MLT1) were tested for its homogenous catalytic activity in Heck cross-coupling reaction. The reaction was monitored by Gas Chromatography-Flame Ionisation Detector (GC-FID). Results reveal that MLT1 exhibits 100% of conversion starting material into a cross-coupling product, which was alkene-based compound.

Bahasa Abstract

Palladium-Tiourea Yang Efisien Sebagai Katalis Reaksi Gandengan Silang Heck Untuk Molekul Elektronik. Sintesis dan penggunaan pembentukan ikatan C-C perlu diperhatikan sebagai langkah utama untuk membina beberapa molekul elektronik terkonduksi yang melibatkan banyak katalis-katalis asimetris, yang merupakan tugas yang sering diabaikan oleh kebanyakan peneliti dalam menyediakan bahan-bahan ini untuk meningkatkan pengeluaran hasil bahan gandengan silang. Meskipun telah banyak perkembangan dalam hal ini, masih ada permintaan yang tinggi untuk proses gandengan silang yang lebih ekonomis dan praktis yang hanya melibatkan pembekalan katalis yang sangat rendah dengan hasil perolehan yang tinggi dengan penggunaan katalis logam biasa. Oleh karena itu, terdapat banyak kepentingan untuk menghasilkan katalis paladium tanpa fosfina untuk pencapaian yang cemerlang dari segi aktivitas, kestabilan dan toleransi substrat yang membenarkan reaksi gandengan silang yang dijalankan dalam keadaan reaksi sederhana pada keadaan atmosfer tertentu. Dalam kajian ini, N-(4-nitrofenilcarbamotionil)-N’-(4-metilbenzoil) tiourea (LT1) dan kompleks logamnya yaitu MLT1 menampilkan Pd(II) telah berhasil dicirikan melalui kaidah spektroskopi yang biasa yaitu spektroskopi sinar inframerah (IR), spektroskopi Ultra-Lembayung Sinar Nampak (UV-Vis), analisis unsur CHNS dan Resonan Magnetik Nukleus (1H dan 13C NMR). Selanjutnya, tindak balas ini dipantau menggunakan Gas Chromatography-Flame Ionisation Detector (GC-FID). Hasil penelitian menunjukkan MLT1 memberikan 100% konversi bahan pemula menjadi produk gandengan silang yaitu senyawa berasaskan alkena.

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Recommended Citation

Khairul, Wan M.; Md Shariff, Mohd Shahrul Shahmi; Rahamathullah, Rafizah; Daud, Adibah Izzati; Shamsuddin, Mustaffa; and Che Soh, Siti Kamilah (2017) "An Efficient Palladium-Thiourea Catalysed Heck Cross-Coupling Reaction for Molecular Electronic Interest," Makara Journal of Technology: Vol. 21: Iss. 2, Article 2.
DOI: 10.7454/mst.v21i2.3081
Available at: https://scholarhub.ui.ac.id/mjt/vol21/iss2/2