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Towards environmentally friendlier Suzuki–Miyaura reactions with precursors of Pd-NHC (NHC = N-heterocyclic carbene) complexes
Green Chemistry ( IF 9.3 ) Pub Date : 2018-05-18 , DOI: 10.1039/c8gc00860d Caroline M. Zinser 1, 2, 3, 4 , Katie G. Warren 1, 2, 3, 4 , Rebecca E. Meadows 4, 5, 6, 7, 8 , Fady Nahra 9, 10, 11, 12 , Abdullah M. Al-Majid 13, 14, 15, 16, 17 , Assem Barakat 13, 14, 15, 16, 17 , Mohammad S. Islam 13, 14, 15, 16, 17 , Steven P. Nolan 9, 10, 11, 12, 13 , Catherine S. J. Cazin 9, 10, 11, 12
Green Chemistry ( IF 9.3 ) Pub Date : 2018-05-18 , DOI: 10.1039/c8gc00860d Caroline M. Zinser 1, 2, 3, 4 , Katie G. Warren 1, 2, 3, 4 , Rebecca E. Meadows 4, 5, 6, 7, 8 , Fady Nahra 9, 10, 11, 12 , Abdullah M. Al-Majid 13, 14, 15, 16, 17 , Assem Barakat 13, 14, 15, 16, 17 , Mohammad S. Islam 13, 14, 15, 16, 17 , Steven P. Nolan 9, 10, 11, 12, 13 , Catherine S. J. Cazin 9, 10, 11, 12
Affiliation
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The preparation of [NHC·H][Pd(η3-R-allyl)Cl2] complexes is disclosed and represents a facile, atom-economical, environmentally friendly and rapid synthesis. These palladates are immediate synthetic precursors to the well-known [Pd(NHC)(η3-R-allyl)Cl] complexes. Their activation leading to catalytically relevant species has been studied in the Suzuki–Miyaura reaction. The need for an activation step prior to the catalysis was examined. The reaction scope showcases its ease and breadth in terms of functional group tolerance. Electron-donating and electron-withdrawing aryl chlorides and bromides were coupled effectively as well as heteroatom-containing and sterically hindered aryl halides. The catalytic reaction was conducted in ethanol with a weak and inexpensive inorganic base.
中文翻译：
寻求与Pd-NHC（NHC = N-杂环卡宾）配合物前体的环境友好型Suzuki-Miyaura反应
的制备[NHC·H] [将Pd（η 3 -R烯丙基）氯2 ]配合物公开并代表一个轻便，原子经济，环保及快速合成。这些palladates是直接合成前体的公知的[将Pd（NHC）（η 3-R-烯丙基）Cl]络合物。在Suzuki-Miyaura反应中已经研究了它们的活化导致相关的催化物种。检查了在催化之前是否需要活化步骤。反应范围从官能团耐受性上展示了它的简便性和广度。给电子和吸电子的芳基氯化物和溴化物以及含杂原子和空间位阻的芳基卤化物均有效耦合。催化反应是在乙醇中用弱且便宜的无机碱进行的。
更新日期：2018-07-16
中文翻译：
寻求与Pd-NHC（NHC = N-杂环卡宾）配合物前体的环境友好型Suzuki-Miyaura反应
的制备[NHC·H] [将Pd（η 3 -R烯丙基）氯2 ]配合物公开并代表一个轻便，原子经济，环保及快速合成。这些palladates是直接合成前体的公知的[将Pd（NHC）（η 3-R-烯丙基）Cl]络合物。在Suzuki-Miyaura反应中已经研究了它们的活化导致相关的催化物种。检查了在催化之前是否需要活化步骤。反应范围从官能团耐受性上展示了它的简便性和广度。给电子和吸电子的芳基氯化物和溴化物以及含杂原子和空间位阻的芳基卤化物均有效耦合。催化反应是在乙醇中用弱且便宜的无机碱进行的。
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