钳形镍化合物的合成、表征及其在Suzuki偶联反应中的应用
摘要
本文利用廉价易得的原料,经“一锅煮”膦化/镍化方法合成了八种钳形镍化合物,并初步考察了该类化合物在Suzuki偶联反应中的催化活性。具体如下：
1、钳形镍化合物2b、5f-h的合成。
分别以间羟基苯甲醛、间苯二胺、邻苯二胺等为原料,采用“一锅煮”膦化/镍化反应制得钳形镍化合物2b、5f-h(Schemes1-3)。
2、钳形镍化合物5i-j的合成。
钳形镍化合物5a和不同当量的NCS反应制得钳形镍化合物5i-j (Scheme4)。
3、钳形镍化合物5k-1的合成。
钳形镍化合物5a经方法a或b可制得钳形镍化合物
4、钳形镍化合物催化性能研究。
初步考察了钳形镍化合物1、2a-c、5a-m在Suzuki偶联反应中的催化活性(Scheme6),结果发现在5a (1mol%)为催化剂、K3PO4为碱、二氧六环为溶剂、PPh3(10mol%)为添加剂、反应24h的条件下,芳基卤代物与芳基硼酸的偶联反应产率较高(>99%)；在1(2mo1%)为催化剂、NaOH为碱、EtOH为溶剂、PPh3(20mol%)为添加剂、反应24h的条件下,甲磺酸芳基酯与芳基硼酸的反应产率较高(>99%)。
Eight pincer-type nickel compounds were accessible from inexpensive and commercially available material by one-pot phosphorylation/nickelation reaction. The catalytic activity of these compounds was investigated in Suzuki coupling reaction.
1. Synthesis of pincer nickel compounds2b、5f-h.
Pincer nickel compounds2b、5f-h were synthesized from m-hydroxy benzaldehyde, m-phenylene diamine, o-phenylendiamine by one-pot phosphorylation/nickelation reaction, respectively (Schemes1-3).
2. Synthesis of pincer nickel compounds5i-j.
Pincer nickel compound5a, reacting with different equivalents of NCS, produced compounds5i-j (Scheme4).
3. Synthesis of pincer nickel compounds5k-l.
Pincer nickel compounds5k-1were obtained from5a through method a or b (Scheme5).
4. Catalytic study of pincer nickel compounds.
Catalytic activity of compounds1,2a-c,5a-m were preliminaryly investigated in Suzuki coupling reaction (Scheme6). In the presence of1mol%5a,0.6equiv K3PO4,10mol%PPh3in dioxane under refluxing for24h, the coupling reaction of aryl halides with aryl boronic acids could obtain up to99%yield. The coupling reaction of methanesulfonic acid aryl esters with aryl boronic acids also yielded up to99%in the presence of2mol%1,0.6equiv NaOH,20mol%PPh3in EtOH and then refluxing for24h.
1、钳形镍化合物2b、5f-h的合成。
分别以间羟基苯甲醛、间苯二胺、邻苯二胺等为原料,采用“一锅煮”膦化/镍化反应制得钳形镍化合物2b、5f-h(Schemes1-3)。
2、钳形镍化合物5i-j的合成。
钳形镍化合物5a和不同当量的NCS反应制得钳形镍化合物5i-j (Scheme4)。
3、钳形镍化合物5k-1的合成。
钳形镍化合物5a经方法a或b可制得钳形镍化合物
4、钳形镍化合物催化性能研究。
初步考察了钳形镍化合物1、2a-c、5a-m在Suzuki偶联反应中的催化活性(Scheme6),结果发现在5a (1mol%)为催化剂、K3PO4为碱、二氧六环为溶剂、PPh3(10mol%)为添加剂、反应24h的条件下,芳基卤代物与芳基硼酸的偶联反应产率较高(>99%)；在1(2mo1%)为催化剂、NaOH为碱、EtOH为溶剂、PPh3(20mol%)为添加剂、反应24h的条件下,甲磺酸芳基酯与芳基硼酸的反应产率较高(>99%)。
Eight pincer-type nickel compounds were accessible from inexpensive and commercially available material by one-pot phosphorylation/nickelation reaction. The catalytic activity of these compounds was investigated in Suzuki coupling reaction.
1. Synthesis of pincer nickel compounds2b、5f-h.
Pincer nickel compounds2b、5f-h were synthesized from m-hydroxy benzaldehyde, m-phenylene diamine, o-phenylendiamine by one-pot phosphorylation/nickelation reaction, respectively (Schemes1-3).
2. Synthesis of pincer nickel compounds5i-j.
Pincer nickel compound5a, reacting with different equivalents of NCS, produced compounds5i-j (Scheme4).
3. Synthesis of pincer nickel compounds5k-l.
Pincer nickel compounds5k-1were obtained from5a through method a or b (Scheme5).
4. Catalytic study of pincer nickel compounds.
Catalytic activity of compounds1,2a-c,5a-m were preliminaryly investigated in Suzuki coupling reaction (Scheme6). In the presence of1mol%5a,0.6equiv K3PO4,10mol%PPh3in dioxane under refluxing for24h, the coupling reaction of aryl halides with aryl boronic acids could obtain up to99%yield. The coupling reaction of methanesulfonic acid aryl esters with aryl boronic acids also yielded up to99%in the presence of2mol%1,0.6equiv NaOH,20mol%PPh3in EtOH and then refluxing for24h.
引文
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