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Tertiary Arsine Ligands for Pd-Catalyzed Direct Arylation
Organometallics ( IF 2.5 ) Pub Date : 2024-01-24 , DOI: 10.1021/acs.organomet.3c00464 Kenta Ogawa 1 , Akifumi Sumida 1 , Takashi Yumura 2 , Hiroaki Imoto 1, 3 , Kensuke Naka 1, 4
Organometallics ( IF 2.5 ) Pub Date : 2024-01-24 , DOI: 10.1021/acs.organomet.3c00464 Kenta Ogawa 1 , Akifumi Sumida 1 , Takashi Yumura 2 , Hiroaki Imoto 1, 3 , Kensuke Naka 1, 4
Affiliation
Catalysts for direct arylations have been extensively studied for the efficient synthesis of (hetero)biaryl compounds. Phosphine ligands are pivotal in this field, and electron-deficient phosphine ligands are advantageous for direct arylation. Due to its relatively weak σ-donation ability, arsenic is considered an ideal candidate for designing electron-deficient ligands. However, no studies have explored the relationship between the structure of the arsine ligands and their catalytic activity for direct arylation. In this study, we synthesized 27 arsine ligands with varying electron-donating and steric properties. Tris(o-trifluorotolyl)arsine, an electron-deficient and bulky ligand, exhibited the highest efficiency in a model reaction between 2-propylthiophene and 4-bromobenzotrifluoride. Both experimental and computational studies revealed the mechanism of direct arylation using arsine ligands. This is the first comprehensive investigation of an arsine-ligated catalytic direct arylation.
中文翻译:
用于 Pd 催化直接芳基化的叔胂配体
为了有效合成(杂)联芳基化合物,直接芳基化催化剂已被广泛研究。膦配体是该领域的关键,缺电子膦配体有利于直接芳基化。由于其相对较弱的σ供体能力,砷被认为是设计缺电子配体的理想候选者。然而,还没有研究探讨胂配体的结构与其直接芳基化催化活性之间的关系。在这项研究中,我们合成了 27 种具有不同给电子和空间特性的胂配体。三(邻三氟甲苯基)胂是一种缺电子且体积大的配体,在2-丙基噻吩和4-溴三氟苯之间的模型反应中表现出最高的效率。实验和计算研究揭示了使用胂配体直接芳基化的机制。这是对胂连接催化直接芳基化的首次全面研究。
更新日期:2024-01-24
中文翻译:
用于 Pd 催化直接芳基化的叔胂配体
为了有效合成(杂)联芳基化合物,直接芳基化催化剂已被广泛研究。膦配体是该领域的关键,缺电子膦配体有利于直接芳基化。由于其相对较弱的σ供体能力,砷被认为是设计缺电子配体的理想候选者。然而,还没有研究探讨胂配体的结构与其直接芳基化催化活性之间的关系。在这项研究中,我们合成了 27 种具有不同给电子和空间特性的胂配体。三(邻三氟甲苯基)胂是一种缺电子且体积大的配体,在2-丙基噻吩和4-溴三氟苯之间的模型反应中表现出最高的效率。实验和计算研究揭示了使用胂配体直接芳基化的机制。这是对胂连接催化直接芳基化的首次全面研究。