大位阻、富电子MOP类配体的合成路线优化及在钯催化碳杂键形成中的应用
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摘要
钯催化下的C-N键形成反应已称为一种多功能的、可靠的、稳定的合成方法。目前现有的催化体系可以催化多种胺与卤代芳烃的偶联反应得到芳胺。然而,如果将该类反应应用到工业化中,还必须提高催化催化剂的催化效率,及提高其反应底物的使用范围,尤其是要开发价格低廉、合成方便、对空气稳定的配体。
本文以廉价的联萘酚为原料,在强酸分子筛条件下脱水得联萘醚,然后通过金属锂锂化得双锂盐,再选择性与二烷基氯化膦反应得到相应的羟基膦化物,继而烷基化得到相应的大位阻和富电子MOP型配体,且此类配体对空气比较稳定。
这类MOP型配体不仅在钯催化简单胺与卤代芳烃尤其是氯代芳烃偶联反应中显示着较高催化活性,并且在与官能化的胺(氨基酸的)偶联中也显示出很好的活性及底物使用范围。可以以较好的产率催化富电子溴代芳烃及氯代芳烃与氨基酸的偶联；并且这个催化体系不仅可以催化α、β氨基酸的偶联,还可以催化γ、δ及苯基的氨基酸的偶联。对于手性的β-氨基酸在偶联反应中手性保持高,产物具有高的ee值。
此外在研究配体合成过程中,我们发现通过金属锂对联萘醚锂化开环,形成双锂盐后,与相应的亲电试剂选择性的反应,可以方便容易的制备应用广泛的2’-位官能化的1,1'-联萘-2-醇类化合物。通过这种方法我们以较好的产率合成了2’-卤代(溴或氯)-1,1'-联萘-2-醇、2'-氨基-1,1'-联萘-2-醇、2'-羟基-1,1'-联萘-2-羧酸(或酯)及2'-羟基-1,1’-联萘-2-膦酸酯。
Palladium-catalyzed C-N bond forming reactions have evolved into a versatile and efficient synthetic transformation. Existing catalyst system showed high activity for assisting the palladium-catalyzed amination of reaction of aryl halides, thus one of the major challenged confronted in the development of more efficient catalysts in inexpensive and simple to synthesis and reading accessible liangds.
A series of 2-dialkylphosphino-2'-alkoxy-1,1'-binaphthyl ligands (6a-c, and 8a-c) have been prepared conveniently by lithium initiated ring-opening reaction of dinaphthofuran, followed by selective phosphorylation. These compounds displayed a remarkable air and moisture stability, both in solid form and in solution.
The bulky and electron-rich MOP-type ligands shows high efficiency for the coupling reaction of amino acids and inactive aryl halides to give N-aryl amino acids. Under the catalytic conditions, not only a-amino acids but alsoβ-,γ, andδ-amino acids have been coupled with aryl chlorides in high yields, in the case of optically pure amino acids as substrates, the coupling products ofβ-amino acids retain high optical purity.
We also developed a simple and efficient one-pot, two step method for synthesis of 2'-functionalized 1, 1'-binaphthyl-2-ols by reductive ring-opening of binaphthofuran (1) with lithium to give the C,O-dilithium reagent (2), followed by reacting it with the corresponding electrophiles to give 2'-functionalized 1, 1'-binaphthyl-2-ols including the halides (3), amine (4), acid (5), aldehyde (6), carbonate (7) or phosphonate (8), respectively, in moderate to good yields.
本文以廉价的联萘酚为原料,在强酸分子筛条件下脱水得联萘醚,然后通过金属锂锂化得双锂盐,再选择性与二烷基氯化膦反应得到相应的羟基膦化物,继而烷基化得到相应的大位阻和富电子MOP型配体,且此类配体对空气比较稳定。
这类MOP型配体不仅在钯催化简单胺与卤代芳烃尤其是氯代芳烃偶联反应中显示着较高催化活性,并且在与官能化的胺(氨基酸的)偶联中也显示出很好的活性及底物使用范围。可以以较好的产率催化富电子溴代芳烃及氯代芳烃与氨基酸的偶联；并且这个催化体系不仅可以催化α、β氨基酸的偶联,还可以催化γ、δ及苯基的氨基酸的偶联。对于手性的β-氨基酸在偶联反应中手性保持高,产物具有高的ee值。
此外在研究配体合成过程中,我们发现通过金属锂对联萘醚锂化开环,形成双锂盐后,与相应的亲电试剂选择性的反应,可以方便容易的制备应用广泛的2’-位官能化的1,1'-联萘-2-醇类化合物。通过这种方法我们以较好的产率合成了2’-卤代(溴或氯)-1,1'-联萘-2-醇、2'-氨基-1,1'-联萘-2-醇、2'-羟基-1,1'-联萘-2-羧酸(或酯)及2'-羟基-1,1’-联萘-2-膦酸酯。
Palladium-catalyzed C-N bond forming reactions have evolved into a versatile and efficient synthetic transformation. Existing catalyst system showed high activity for assisting the palladium-catalyzed amination of reaction of aryl halides, thus one of the major challenged confronted in the development of more efficient catalysts in inexpensive and simple to synthesis and reading accessible liangds.
A series of 2-dialkylphosphino-2'-alkoxy-1,1'-binaphthyl ligands (6a-c, and 8a-c) have been prepared conveniently by lithium initiated ring-opening reaction of dinaphthofuran, followed by selective phosphorylation. These compounds displayed a remarkable air and moisture stability, both in solid form and in solution.
The bulky and electron-rich MOP-type ligands shows high efficiency for the coupling reaction of amino acids and inactive aryl halides to give N-aryl amino acids. Under the catalytic conditions, not only a-amino acids but alsoβ-,γ, andδ-amino acids have been coupled with aryl chlorides in high yields, in the case of optically pure amino acids as substrates, the coupling products ofβ-amino acids retain high optical purity.
We also developed a simple and efficient one-pot, two step method for synthesis of 2'-functionalized 1, 1'-binaphthyl-2-ols by reductive ring-opening of binaphthofuran (1) with lithium to give the C,O-dilithium reagent (2), followed by reacting it with the corresponding electrophiles to give 2'-functionalized 1, 1'-binaphthyl-2-ols including the halides (3), amine (4), acid (5), aldehyde (6), carbonate (7) or phosphonate (8), respectively, in moderate to good yields.
引文
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