THE OXIDATIVE CROSS-COUPLING OF SUBSTITUTED 2-NAPHTHOLS .1. THE SCOPE AND LIMITATIONS
THE OXIDATIVE CROSS-COUPLING OF SUBSTITUTED 2-NAPHTHOLS .1. THE SCOPE AND LIMITATIONS
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DOI：
10.1016/s0040-4020(01)88318-6
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发表时间：
1992-10-23
期刊：
影响因子：
2.1
通讯作者：
ZAVADA, J
中科院分区：
文献类型：
--
作者：
HOVORKA, M;SCIGEL, R;ZAVADA, J
描述了由Cu（II）-叔丁胺络合物介导的不同取代的2-萘酚的高选择性氧化交叉偶联。“交叉”产物以良好至优异的产率获得，并且观察到高达>90%的选择性取决于萘酚核的取代。的替代程序的交叉耦合的游离萘酚与CuCl（OMe），以及耦合的萘酚钠与无水氯化铜（II）-也进行了研究。所有这些方法使得简单和高产率地获得不对称取代的联萘酚。本文报道用三乙酰纤维素液相色谱法成功地拆分了2，2 ′-二羟基-1，1 ′-联萘-3-羧酸甲酯，并与已知绝对构型的联萘衍生物进行了构型关联。
Highly selective oxidative cross-coupling of differently substituted 2-naphthols mediated by Cu(II)-tert-butyl amine complexes is described. The "cross"-products are obtained in good to excellent yields and the selectivity up to >90% is observed depending on the substitution of naphthol nuclei. The alternative procedures-the cross-coupling of free naphthols with CuCl(OMe) as well as the coupling of sodium naphtholates with anhydrous copper(II) chloride -were also studied. All these methods enable a simple and high-yield access to the unsymmetrically substituted binaphthols. A successful optical resolution of methyl 2,2'-dihydroxy-1,1'-binaphthalene-3-carboxylate by means of liquid chromatography on triacetylcellulose and the subsequent configurational correlation with a binaphthol derivative of known absolute configuration is reported.