Nickel-Catalyzed Cross-Coupling of Diarylborinic Acids with Aryl Chlorides
Nickel-Catalyzed Cross-Coupling of Diarylborinic Acids with Aryl Chlorides
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DOI：
10.1021/cs4009946
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发表时间：
2014-02-01
期刊：
影响因子：
12.9
通讯作者：
Zou, Gang
中科院分区：
文献类型：
--
作者：
Chen, Xiaofeng;Ke, Haihua;Zou, Gang
本文报道了一种高效的镍/三芳基膦催化体系Ni[P（4-MeOPh）（3）]（2）Cl-2/2 P（4-MeOPh）（3），用于二芳基硼酸与多种芳基氯的偶联反应。在K_3PO_4中心点~ 3 H（2）O存在下，催化剂用量为0.5 ~ 2mol%时，甲苯中可得到多种具有不同官能团和空间位阻的不对称联芳基和杂联芳基化合物，产率良好。二芳基硼酸的高原子经济性和镍/膦催化剂体系的成本效益使得交叉偶联在联芳基精细化学品的生产中真正实用。镍/膦催化的二芳基硼酸与芳基氯的交叉偶联的可行性已经在用于合成4 '-甲基-2-氰基联苯、沙坦联苯的可扩展且经济的方法的开发中得到证实。
A highly efficient nickel/triarylphosphine catalyst system, Ni[P(4-MeOPh)(3)](2)Cl-2/2P(4-MeOPh)(3), has been developed for cross-coupling of diarylborinic acids with a wide range of aryl chlorides. A variety of unsymmetrical biaryl and heterobiaryl compounds with various functional groups and steric hindrance could be obtained in good to excellent yields using 0.5-2 mol % catalyst loadings in the presence of K3PO4 center dot 3H(2)O in toluene. The high atom economy of diarylborinic acids and cost-effectiveness of the nickel/phosphine catalyst system make the cross-coupling truly practical in the production of biaryl fine chemicals. Usefulness of the nickel/phosphine catalyzed cross-coupling of diarylborinic acids with aryl chlorides has been demonstrated in the development of a scalable and economical process for synthesis of 4'-methyl-2-cyanobiphenyl, Sartan biphenyl.