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Design and Syntheses of Palladium Complexes of NNN/CNN Pincer Ligands: Catalyst for Cross Dehydrogenative Coupling Reaction of Heteroarenes
Organometallics ( IF 2.5 ) Pub Date : 2020-01-13 , DOI: 10.1021/acs.organomet.9b00695 Vikki N. Shinde 1 , Nattamai Bhuvanesh 2 , Anil Kumar 1 , Hemant Joshi 3
Organometallics ( IF 2.5 ) Pub Date : 2020-01-13 , DOI: 10.1021/acs.organomet.9b00695 Vikki N. Shinde 1 , Nattamai Bhuvanesh 2 , Anil Kumar 1 , Hemant Joshi 3
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This report describes simple syntheses of a new class of palladium(II) pincer complexes having NNN and CNN coordination modes. The new complexes were fully characterized with the help of 1H and 13C{1H} NMR, HRMS, and IR spectroscopy. The structure and bonding modes of complexes were further authenticated with the help of single-crystal X-ray diffraction. Thermally robust and moisture-/air-insensitive palladium pincer complexes C1–C4 have been used as catalysts for cross dehydrogenative coupling (CDC) reactions of two heteroarenes and found to be very efficient. The catalyst was successful in activating the C–H bond of a variety of heteroarenes, including benzimidazole, imidazole, benzothiazole, imidazopyridine, thiophene, and furan, with only 1.0 mol % of catalyst, achieving excellent yields of the coupled products. The catalyst showed excellent tolerance toward functional groups such as CHO, COMe, COOMe, COOEt, CONHPh, Me, CN, Br, and Cl. Further, the catalyst is reusable up to four reaction cycles with only a minor loss in its efficiency. The mechanism of the CDC reaction was investigated through control experiments, and it has been suggested that a palladium acetate analogue of the NNN pincer ligand (C5) is the active catalyst.
中文翻译：
NNN / CNN钳形配体的钯配合物的设计与合成：杂芳烃交叉脱氢偶联反应的催化剂
该报告描述了具有NNN和CNN配位模式的新型钯（II）钳形配合物的简单合成。借助1 H和13 C { 1 H} NMR，HRMS和IR光谱对新配合物进行了全面表征。借助单晶X射线衍射进一步验证了配合物的结构和键合模式。具有热稳定性且对湿气/空气不敏感的钯夹钳复合物C1 - C4已被用作两个杂芳烃的交叉脱氢偶联（CDC）反应的催化剂，发现非常有效。该催化剂仅用1.0 mol％的催化剂即可成功活化包括苯并咪唑，咪唑，苯并噻唑，咪唑并吡啶，噻吩和呋喃在内的多种杂芳烃的C–H键，仅偶联剂的收率就很高。该催化剂对CHO，COMe，COOMe，COOEt，CONHPh，Me，CN，Br和Cl等官能团具有极好的耐受性。此外，该催化剂可重复使用多达四个反应周期，而效率仅有很小的损失。通过控制实验研究了CDC反应的机理，已表明NNN钳形配体（C5）的乙酸钯类似物是活性催化剂。
更新日期：2020-01-14
中文翻译：
NNN / CNN钳形配体的钯配合物的设计与合成：杂芳烃交叉脱氢偶联反应的催化剂
该报告描述了具有NNN和CNN配位模式的新型钯（II）钳形配合物的简单合成。借助1 H和13 C { 1 H} NMR，HRMS和IR光谱对新配合物进行了全面表征。借助单晶X射线衍射进一步验证了配合物的结构和键合模式。具有热稳定性且对湿气/空气不敏感的钯夹钳复合物C1 - C4已被用作两个杂芳烃的交叉脱氢偶联（CDC）反应的催化剂，发现非常有效。该催化剂仅用1.0 mol％的催化剂即可成功活化包括苯并咪唑，咪唑，苯并噻唑，咪唑并吡啶，噻吩和呋喃在内的多种杂芳烃的C–H键，仅偶联剂的收率就很高。该催化剂对CHO，COMe，COOMe，COOEt，CONHPh，Me，CN，Br和Cl等官能团具有极好的耐受性。此外，该催化剂可重复使用多达四个反应周期，而效率仅有很小的损失。通过控制实验研究了CDC反应的机理，已表明NNN钳形配体（C5）的乙酸钯类似物是活性催化剂。
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