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Synthesis, Characterization, and Catalytic Studies of Unsymmetrical Chiral NCC Pincer Pd(II) and Ni(II) Complexes Bearing (Imidazolinyl)aryl NHC Ligands
Organometallics ( IF 2.5 ) Pub Date : 2018-07-03 , DOI: 10.1021/acs.organomet.8b00300 Jing Yan 1 , Yan-Bing Wang 1 , Zhi-Hui Zhu 1 , Yigao Li 1 , Xinju Zhu 1 , Xin-Qi Hao 1 , Mao-Ping Song 1
Organometallics ( IF 2.5 ) Pub Date : 2018-07-03 , DOI: 10.1021/acs.organomet.8b00300 Jing Yan 1 , Yan-Bing Wang 1 , Zhi-Hui Zhu 1 , Yigao Li 1 , Xinju Zhu 1 , Xin-Qi Hao 1 , Mao-Ping Song 1
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A series of palladium(II) and nickel(II) complexes based on unsymmetrical chiral (imidazolinyl)aryl NHC ligands are reported. The new ligand presursors 3a–g were prepared from commercially available 3-bromobenzoic acid, in which the carboxyl and bromo functionalities were converted to chiral imidazoline and NHC moieties, respectively, in three steps. Treatment of 3a–g with Pd(OAc)2 in dimethylacetamide in the presence of NaOAc, followed by addition of LiCl, gave the seven palladium(II) pincer complexes 4a–g via direct aryl C–H activation. Likewise, the six nickel(II) pincer complexes 5a–f were obtained by reacting 3a–f with anhydrous NiCl2. All of the ligand precursors and pincer complexes are bench-stable and were fully characterized. The absolute configurations of palladium complexes 4a,c and 5e were further determined by X-ray diffraction. Finally, Pd pincer complex catalyzed asymmetric Friedel–Crafts alkylation and aza-Morita–Baylis–Hillman reactions were briefly assessed.
中文翻译：
含（咪唑啉基）芳基NHC配体的不对称手性NCC夹钳Pd（II）和Ni（II）配合物的合成，表征和催化研究
报道了基于不对称手性（咪唑啉基）芳基NHC配体的一系列钯（II）和镍（II）配合物。新的配体前体化合物3a – g由可商购的3-溴苯甲酸制备，其中羧基和溴代官能团通过三个步骤分别转化为手性咪唑啉和NHC部分。在NaOAc存在下，用Pd（OAc）2在二甲基乙酰胺中的Pd（OAc）2处理3a – g，然后添加LiCl，通过直接的芳基C–H活化得到七个钯（II）钳形配合物4a – g。同样，六个镍（II）钳形络合物5a – f通过3a - f与无水NiCl 2反应获得。所有的配体前体和钳状复合物都是台式稳定的，并且已得到充分表征。钯配合物4a，c和5e的绝对构型通过X射线衍射进一步确定。最后，简要评估了Pd钳配合物催化的不对称Friedel-Crafts烷基化反应和aza-Morita-Baylis-Hillman反应。
更新日期：2018-07-04
中文翻译：
含（咪唑啉基）芳基NHC配体的不对称手性NCC夹钳Pd（II）和Ni（II）配合物的合成，表征和催化研究
报道了基于不对称手性（咪唑啉基）芳基NHC配体的一系列钯（II）和镍（II）配合物。新的配体前体化合物3a – g由可商购的3-溴苯甲酸制备，其中羧基和溴代官能团通过三个步骤分别转化为手性咪唑啉和NHC部分。在NaOAc存在下，用Pd（OAc）2在二甲基乙酰胺中的Pd（OAc）2处理3a – g，然后添加LiCl，通过直接的芳基C–H活化得到七个钯（II）钳形配合物4a – g。同样，六个镍（II）钳形络合物5a – f通过3a - f与无水NiCl 2反应获得。所有的配体前体和钳状复合物都是台式稳定的，并且已得到充分表征。钯配合物4a，c和5e的绝对构型通过X射线衍射进一步确定。最后，简要评估了Pd钳配合物催化的不对称Friedel-Crafts烷基化反应和aza-Morita-Baylis-Hillman反应。
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