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Synthesis and hydroformylation evaluation of Fréchet-type organometallic dendrons with N,O-salicylaldimine Rh(i) complexes at the focal point†
Dalton Transactions ( IF 3.5 ) Pub Date : 2018-06-20 00:00:00 , DOI: 10.1039/c8dt01874j Cody Williams 1, 2, 3, 4 , Michel Ferreira 5, 6, 7, 8, 9 , Eric Monflier 5, 6, 7, 8, 9 , Selwyn F. Mapolie 4, 10, 11, 12 , Gregory S. Smith 1, 2, 3, 4
Dalton Transactions ( IF 3.5 ) Pub Date : 2018-06-20 00:00:00 , DOI: 10.1039/c8dt01874j Cody Williams 1, 2, 3, 4 , Michel Ferreira 5, 6, 7, 8, 9 , Eric Monflier 5, 6, 7, 8, 9 , Selwyn F. Mapolie 4, 10, 11, 12 , Gregory S. Smith 1, 2, 3, 4
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A series of organometallic dendrons containing N,O-salicylaldimine entities at the focal point were synthesised by reacting the N,O-salicylaldimine-functionalised Fréchet dendrons (G0, G1 and G2) with a [Rh(μ-Cl)(η2:η2-COD)]2 dimer to yield the corresponding Rh(COD) [COD = cyclooctadiene] complexes. These Rh(COD) complexes were exposed to an atmosphere of CO to yield a new class of rhodium carbonyl organometallic dendrons with Rh(CO)2 units at the focal point. All the compounds were characterised using standard spectroscopic and analytical techniques, these include nuclear magnetic resonance, infrared spectroscopy, mass spectrometry and single-crystal X-ray diffraction for compounds 1, 4 and 7. All of the complexes were evaluated in the hydroformylation of 1-octene, with excellent conversion and chemoselectivity towards aldehydes. The G0-(CO)2 catalyst precursor (7) was active in the hydroformylation of 1-octene, styrene, 7-tetradecene, methyl oleate, triolein, D-limonene and R-citronellal. The conversion and chemoselectivity towards aldehydes for 7-tetradecene, methyl oleate, triolein and D-limonene were promising. Across a particular dendron series, an increase in chemoselectivity was observed due to the dendritic effect. Mercury drop tests were performed for the G0-analogues and these confirm that the hydroformylation can be attributed to a combination of homogeneous and heterogeneous catalysis.
中文翻译：
焦点处 具有N，O-水杨醛亚胺Rh（i）配合物的Fréchet型有机金属树枝状分子的合成和加氢甲酰化评估†
将含有有机金属系列的树突Ñ，ö -salicylaldimine实体在焦点处是由反应合成Ñ，ö -salicylaldimine官能Fréchet可树突（G 0，G 1和G 2）用的[Rh（μ-Cl）的（ η 2：η 2 -COD）] 2二聚体，得到相应的Rh（COD）[COD =环辛二烯]络合物。将这些Rh（COD）络合物暴露于CO气氛中，以产生具有Rh（CO）2的新型羰基铑有机金属树突联络点的单位。使用标准光谱和分析技术所有化合物进行了表征，这些包括核磁共振，红外光谱，质谱和对化合物的单晶X射线衍射1，4和7。所有的配合物均在1-辛烯的加氢甲酰化反应中进行了评估，具有出色的转化率和对醛的化学选择性。G 0-（CO）2催化剂前体（7）在1-辛烯，苯乙烯，7-十四烯，油酸甲酯，三油精，D-柠檬烯和R的加氢甲酰化中具有活性。-香茅油。7-十四烯，油酸甲酯，三油精和D-柠檬烯对醛的转化率和化学选择性是有希望的。在整个特定树突系列中，由于树突效应，观察到化学选择性的增加。对G 0-类似物进行了汞滴试验，这些试验证实加氢甲酰化可归因于均相和非均相催化的组合。
更新日期：2018-06-20
中文翻译：
焦点处 具有N，O-水杨醛亚胺Rh（i）配合物的Fréchet型有机金属树枝状分子的合成和加氢甲酰化评估†
将含有有机金属系列的树突Ñ，ö -salicylaldimine实体在焦点处是由反应合成Ñ，ö -salicylaldimine官能Fréchet可树突（G 0，G 1和G 2）用的[Rh（μ-Cl）的（ η 2：η 2 -COD）] 2二聚体，得到相应的Rh（COD）[COD =环辛二烯]络合物。将这些Rh（COD）络合物暴露于CO气氛中，以产生具有Rh（CO）2的新型羰基铑有机金属树突联络点的单位。使用标准光谱和分析技术所有化合物进行了表征，这些包括核磁共振，红外光谱，质谱和对化合物的单晶X射线衍射1，4和7。所有的配合物均在1-辛烯的加氢甲酰化反应中进行了评估，具有出色的转化率和对醛的化学选择性。G 0-（CO）2催化剂前体（7）在1-辛烯，苯乙烯，7-十四烯，油酸甲酯，三油精，D-柠檬烯和R的加氢甲酰化中具有活性。-香茅油。7-十四烯，油酸甲酯，三油精和D-柠檬烯对醛的转化率和化学选择性是有希望的。在整个特定树突系列中，由于树突效应，观察到化学选择性的增加。对G 0-类似物进行了汞滴试验，这些试验证实加氢甲酰化可归因于均相和非均相催化的组合。
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