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Synthesis of tetranuclear complex of Pd(II) with thiosemicarbazone ligands derived from 2-quinolone and its catalytic evaluation in Suzuki–Miyaura-type coupling reactions and alkoxylation of chloroquinolines
Applied Organometallic Chemistry ( IF 3.7 ) Pub Date : 2021-09-03 , DOI: 10.1002/aoc.6436 Sundar Nandhini 1 , Sivadasan Dharani 1 , Chennakrishnan Elamathi 1 , Frederic Dallemer 2 , Rathinasabapathi Prabhakaran 1
Applied Organometallic Chemistry ( IF 3.7 ) Pub Date : 2021-09-03 , DOI: 10.1002/aoc.6436 Sundar Nandhini 1 , Sivadasan Dharani 1 , Chennakrishnan Elamathi 1 , Frederic Dallemer 2 , Rathinasabapathi Prabhakaran 1
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A tetranuclear palladium(II) complex [(Pd(H-6MOQtsc-Ph))4] was obtained from the reaction between 6-methyl-2-oxo-1,2-dihydroquinoline-3-carboxaldehyde-4(N)-phenylthiosemicarbazone [H2-6MOQtsc-Ph] and K2[PdCl4]. The ligand and the Pd(II) complex were characterized by Fourier transform infrared spectroscopy (FT-IR), UV–visible and 1H NMR spectroscopy. X-ray diffraction studies confirmed the tetrameric nature of the complex with the coordination of ligand through quinolone carbonyl, azomethine nitrogen and thiolate sulfur atoms, and the fourth site is occupied by 2-quinolone nitrogen atom of the adjacent ligand. The synthesized complex was tested as catalyst in Suzuki–Miyaura coupling reaction between various chloroquinoline derivatives with phenylboronic acid. The reactions afforded unexpected C-alkoxylated (CO coupling) products instead of more expected C-arylated (CC coupling) products in the respective alcoholic mediums. However, the reactions with traditional aryl halides probed with very good yield of the corresponding CC coupling products.
中文翻译：
2-喹诺酮衍生的 Pd(II) 与缩氨基硫脲配体的四核配合物的合成及其在 Suzuki-Miyaura 型偶联反应和氯喹啉烷氧基化中的催化评价
6-methyl-2-oxo-1,2-dihydroquinoline-3-carboxaldehyde-4( N ) -phenylthiosemicarbazone反应得到四核钯(II)配合物[(Pd(H-6MOQtsc-Ph)) 4 ] [H 2 -6MOQtsc-Ph]和 K 2 [PdCl 4 ]。配体和 Pd(II) 配合物通过傅里叶变换红外光谱 (FT-IR)、紫外-可见光和1核磁共振谱。X 射线衍射研究证实了配合物通过喹诺酮羰基、偶氮甲碱氮和硫醇盐硫原子与配体配位的四聚体性质，第四位点被相邻配体的 2-喹诺酮氮原子占据。合成的配合物在各种氯喹啉衍生物与苯基硼酸之间的 Suzuki-Miyaura 偶联反应中作为催化剂进行了测试。这些反应在各自的醇介质中提供了意想不到的 C-烷氧基化（C O 偶联）产物，而不是更多预期的 C-芳基化（C C 偶联）产物。然而，与传统芳基卤化物的反应以非常好的相应 C C 偶联产物的产率探测。
更新日期：2021-09-03
中文翻译：
2-喹诺酮衍生的 Pd(II) 与缩氨基硫脲配体的四核配合物的合成及其在 Suzuki-Miyaura 型偶联反应和氯喹啉烷氧基化中的催化评价
6-methyl-2-oxo-1,2-dihydroquinoline-3-carboxaldehyde-4( N ) -phenylthiosemicarbazone反应得到四核钯(II)配合物[(Pd(H-6MOQtsc-Ph)) 4 ] [H 2 -6MOQtsc-Ph]和 K 2 [PdCl 4 ]。配体和 Pd(II) 配合物通过傅里叶变换红外光谱 (FT-IR)、紫外-可见光和1核磁共振谱。X 射线衍射研究证实了配合物通过喹诺酮羰基、偶氮甲碱氮和硫醇盐硫原子与配体配位的四聚体性质，第四位点被相邻配体的 2-喹诺酮氮原子占据。合成的配合物在各种氯喹啉衍生物与苯基硼酸之间的 Suzuki-Miyaura 偶联反应中作为催化剂进行了测试。这些反应在各自的醇介质中提供了意想不到的 C-烷氧基化（C O 偶联）产物，而不是更多预期的 C-芳基化（C C 偶联）产物。然而，与传统芳基卤化物的反应以非常好的相应 C C 偶联产物的产率探测。
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