CN100415755C - 2,2’,6,6’-四取代氮膦配体及其合成方法 - Google Patents
2,2’,6,6’-四取代氮膦配体及其合成方法 Download PDFInfo
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/46—Phosphinous acids [R2POH], [R2P(= O)H]: Thiophosphinous acids including[R2PSH]; [R2P(=S)H]; Aminophosphines [R2PNH2]; Derivatives thereof
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Abstract
本发明涉及一种2,2’,6,6’-四取代氮膦配体及其合成方法。配体的结构式如下,其合成包括三步反应:第一步,2,6-二硝基氯苯为起始原料,经偶联后得到2,2’,6,6’-四硝基联苯;第二步,2,2’,6,6’-四硝基联苯经过钯碳加氢得到2,2’,6,6’-四氨基联苯;第三步,2,2’,6,6’-四氨基联苯与二苯基磷氯反应得到2,2’,6,6’-四二苯基膦基胺基联苯。本发明的配体本身是一类没有手性的化合物,此配体制备方法简便,并且最终可以通过引入外加手性得到单一构型的双金属手性催化剂。并且可以应用于多种金属催化的不对称反应中,具有很高的反应活性和立体选择性。
Description
技术领域
本发明涉及一种非手性配体及其合成方法,具体涉及一种用于不对称催化反应中的2,2’,6,6’-四取代氮膦配体及其合成方法。
技术背景
不对称催化方式是获得单一对映异构体的手性药物的较佳的途径,可实现由少量手性催化剂得到大量手性化合物,减少甚至避免无效体的生成,既有利于环保,又能达到好的原子经济性,还可以避开对外消旋体的繁琐拆分。
设计和合成高选择性和高催化活性的手性催化剂是不对称催化合成的关键所在。而在过渡金属催化的不对称反应中与金属配位的手性配体对反应活性及对映选择性起着决定性作用。
自从轴手性配体BINAP问世以来,具有联苯或联萘骨架的配体得到了人们的普遍关注。主要是由于结构柔性的联苯或联萘骨架可沿轴向自由旋转,由其衍生出的催化体系在这一领域也取得了相当好的结果。
另一方面,大多数不对称催化反应体系只存在一个催化中心,通过底物与试剂与之配位而达到活化,在配体的手性环境影响下,形成热力学稳定的过渡态,并最终实现不对称诱导。最近,对于双金属配体,人们也给予了很大的关注。双金属配体可以作为有机金属的一个新的骨架,通过两个金属的协调发挥作用,对于很多反应都提供了很好的化学选择性和对映选择性。因此,双金属轴手性配体的开发已经渐渐成为学术界和产业界关注的重点研究领域。
经对现有技术的文献检索发现,至今尚未发现与本发明主题相同或者类似的文献报道。
发明内容
本发明提出了一种2,2’,6,6’-四取代氮膦配体及其合成方法,该配体可应用于多种金属催化的不对称反应中,具有很高的反应活性和立体选择性,它有别于其他的双金属配体的是:此配体本身是一类没有手性的化合物,制备方法简便,并且最终可以通过引入外加手性得到单一构型的双金属手性催化剂。
本发明是通过以下技术方案实现的,本发明所述的2,2’,6,6’-四取代氮膦配体,即2,2’,6,6’--四二苯基膦基胺基联苯,结构式如下:
本发明还提供上述的2,2’,6,6’--四二苯基膦基胺基联苯的合成方法,包括三步反应:
第一步,2,6-二硝基氯苯为起始原料,经偶联后得到2,2’,6,6’-四硝基联苯;
第二步,2,2’,6,6’-四硝基联苯经过钯碳加氢得到2,2’,6,6’-四氨基联苯;
第三步,2,2’,6,6’-四氨基联苯与二苯基磷氯反应得到2,2’,6,6’-四二苯基膦基胺基联苯。
本发明方法反应式如下:
所述的第一步反应,具体为:用固相反应法,将1当量的2,6-二硝基氯苯和3当量的铜粉混合,在180℃下剧烈搅拌下反应,用乙酸乙酯洗涤,过滤沉淀,滤液浓缩,用乙酸乙酯,石油醚的混合溶液重结晶。
所述的第二步反应,具体为:以底物质量10%钯碳为催化剂,加入到2,2’,6,6’-四硝基联苯中,在高压釜中加入10个大气压的氢气,反应结束后,滤除固体,滤液浓缩得2,2’,6,6’-四氨基联苯。
所述的第三步反应,具体为:以二氯甲烷或四氢呋喃为溶剂,以三乙胺或丁基锂为碱,在1当量的2,2’,6,6’-四氨基联苯中加入5当量二苯基膦氯,反应得到2,2’,6,6’-四二苯基膦基胺基联苯。
本发明2,2’,6,6’-四二苯基膦基胺基联苯含有四个配位中心。该类配体可应用于各种金属催化的不对称反应中,如酮的不对称加氢,不对称环丙烷化反应,分子内Wacker-Type环化反应,烯烃的不对称氧化反应和分子内[2+1]环加成反应等,具有很高的反应活性和立体选择性,具有较好的应用前景。
具体实施方式
以下结合本发明的技术内容提供实施例:
实施例一
1.2,2’,6,6’-四硝基联苯的制备
预处理铜粉:称取铜粉(5.0g,78mmol)加入到2%的碘/丙酮溶液20ml中,搅拌十分钟,抽滤,再加入到丙酮∶盐酸=1∶1的混合溶液20ml中,搅拌十分钟,抽滤,真空干燥。在250ml圆底烧瓶中加入2,6-二硝基氯苯(3.04g,15mmol)和铜粉(2.88g,45mmol)混和均匀,在氮气保护下,油浴加热至180℃下搅拌2小时。反应结束后,将瓶中固体倒碎,用20ml乙酸乙酯溶解,过滤出固体,收集滤液,旋蒸。用乙酸乙酯∶石油醚=10∶1重结晶,析出浅黄色针状晶体,抽滤,收集晶体,即为产物,产率63.9%。
1H NMR(400 MHz,CDCl3):7.89(t,2H,J=8.0Hz,ArH),8.51(d,4H,J=8.0Hz,ArH)。
熔点:217℃-218℃
2.2,2’,6,6’-四氨基联苯的制备
氮气保护,在100ml氢化瓶中,加入2,2’,6,6’-四硝基联苯(1.00g,3mmol)和100mg10%的Pd/C,再加入20ml甲醇,用氮气鼓泡。将氢化瓶放入高压釜中,加入10atm的氢气。6小时后,反应结束,过滤除去Pd/C,旋蒸甲醇,乙酸乙酯,水萃取,无水硫酸钠干燥,过滤,旋蒸,产率88%。
1H NMR(400 MHz,CDCl3):6.99(t,2H,J=8.0Hz,ArH),6.25(d,4H,J=8.0Hz,ArH),3.3-3.8(brs,8H,NH)
熔点:204℃。
3.2,2’,6,6’-四二苯基膦基胺基联苯的制备
2,2’,6,6’-四氨基联苯(107.90mg,0.5mmmol)溶于10ml二氯甲烷中,再把三乙胺(0.56ml,4mmol),二苯基邻氯(0.45ml,2.5mmol)依次逐滴加入其中。50℃下回流搅拌24小时。溶液冷却,浓缩,加入5ml无水乙醚,过滤沉淀,并用5ml无水乙醚洗涤。乙酸乙酯/石油醚=1∶5柱层析,得目标产物,产率76%。
1H NMR(400 MHz,CDCl3):7.09-7.21(m,44H,ArH),6.87(d,2H,J=2.8Hz,ArH),6.86(d,2H,J=2.8Hz,ArH),4.53(d,4H,J=5.2Hz,NH)。
实施例二:
1.2,2’,6,6’-四硝基联苯的制备(同实施例一)
2.2,2’,6,6’-四氨基联苯的制备(同实施例一)
3.2,2’,6,6’-四二苯基磷基氨基联苯的制备
2,2’,6,6’-四氨基联苯(107.90mg,0.5mmol)溶于10ml四氢呋喃中,反应体系冷至-30℃,向体系中逐滴加入正丁基锂的正己烷溶液(2.57M,0.78ml),并且在此温度下搅拌2小时后,再逐滴加入二苯基邻氯(0.45ml,2.5mmol),温度升至25℃,搅拌5小时,过滤沉淀,蒸去四氢呋喃。乙酸乙酯/石油醚=1∶5柱层析,得目标产物,产率83%。
Claims (5)
2. 一种如权利要求1所述的2,2’,6,6’-四取代氮膦配体的合成方法,其特征在于,包括三步反应:
第一步,2,6-二硝基氯苯为起始原料,经偶联后得到2,2’,6,6’-四硝基联苯;
第二步,2,2’,6,6’-四硝基联苯经过钯碳加氢得到2,2’,6,6’-四氨基联苯;
第三步,2,2’,6,6’-四氨基联苯与二苯基膦氯反应得到2,2’,6,6’-四二苯基膦基胺基联苯。
3. 根据权利要求2所述的2,2’,6,6’-四取代氮膦配体的合成方法,其特征是,所述的第一步反应,具体为:用固相反应法,将1当量的2,6-二硝基氯苯和3当量的铜粉混合,在180℃下剧烈搅拌下反应,用乙酸乙酯洗涤,过滤沉淀,滤液浓缩,用乙酸乙酯,石油醚的混合溶液重结晶。
4. 根据权利要求2所述的2,2’,6,6’-四取代氮膦配体的合成方法,其特征是,所述的第二步反应,具体为:以底物质量10%钯碳为催化剂,加入到2,2’,6,6’-四硝基联苯中,在高压釜中加入10个大气压的氢气,反应结束后,过滤固体,滤液浓缩得2,2’,6,6’-四氨基联苯。
5. 根据权利要求2所述的2,2’,6,6’-四取代氮膦配体的合成方法,其特征是,所述的第三步反应,具体为:以二氯甲烷或四氢呋喃为溶剂,以三乙胺或丁基锂为碱,在1当量的2,2’,6,6’-四氨基联苯中加入5当量二苯基膦氯,反应得到2,2’,6,6’-四二苯基膦基胺基联苯。
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US12/377,000 US8729303B2 (en) | 2006-08-10 | 2007-08-10 | 2,2′,6,6′-tetrasubstituted aminophosphine ligand and its synthesis method |
JP2009523140A JP5208939B2 (ja) | 2006-08-10 | 2007-08-10 | 2,2’,6,6’−四置換アミノホスフィン配位子及びその合成方法 |
PCT/CN2007/002407 WO2008019598A1 (fr) | 2006-08-10 | 2007-08-10 | Ligand aminophosphine 2,2',6,6'-tétrasubstitué et son procédé de synthèse |
CNA2007800297834A CN101528757A (zh) | 2006-08-10 | 2007-08-10 | 2,2’,6,6’-四取代氮膦配体及其合成方法 |
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CN101648977B (zh) * | 2009-09-10 | 2013-04-24 | 上海交通大学 | 2,2’,6,6’位连接的1,1’-联苯类轴手性双亚膦酰胺配体及其制备方法 |
CN113651855B (zh) * | 2021-08-19 | 2023-08-22 | 东北师范大学 | 一种新型负载结晶性多孔骨架材料及其制备方法和应用 |
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NEWATROPISOMERICCHIRALBISPHOSPHINE,(S)-6,6'-DIMETHYL-2,2'-BIS(DIPHENYLPHOSPHINAMINO)BIPHENYL, AND ASYMMETRICHYDROGENATION USING THE Rh(I) COMPLEX THEREOF. Akira UEHARA,et al.CHEMISTRY LETTERS. 1983 |
NEWATROPISOMERICCHIRALBISPHOSPHINE,(S)-6,6'-DIMETHYL-2,2'-BIS(DIPHENYLPHOSPHINAMINO)BIPHENYL, AND ASYMMETRICHYDROGENATION USING THE Rh(I) COMPLEX THEREOF. Akira UEHARA,et al.CHEMISTRY LETTERS. 1983 * |
Ullmann Synthesis of Six Dimethyldinitrobiphenyls and theirReduction to the Corresponding Diaminodimethylbiphenyls. ROBERT B.CARLIN,et al.Journal of the American Chemical Society,Vol.78 No.9. 1956 |
Ullmann Synthesis of Six Dimethyldinitrobiphenyls and theirReduction to the Corresponding Diaminodimethylbiphenyls. ROBERT B.CARLIN,et al.Journal of the American Chemical Society,Vol.78 No.9. 1956 * |
手性膦配体的合成及其在不对称催化反应中的应用研究进展. 徐利文等.有机化学,第23卷第9期. 2003 |
手性膦配体的合成及其在不对称催化反应中的应用研究进展. 徐利文等.有机化学,第23卷第9期. 2003 * |
硝基苯加氢制备苯胺的催化体系研究进展. 郭延红等.化学工程师,第2期. 2004 |
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JP5208939B2 (ja) | 2013-06-12 |
WO2008019598A1 (fr) | 2008-02-21 |
CN101528757A (zh) | 2009-09-09 |
CN1911940A (zh) | 2007-02-14 |
JP2010500295A (ja) | 2010-01-07 |
US8729303B2 (en) | 2014-05-20 |
US20100217040A1 (en) | 2010-08-26 |
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