镍催化的烯丙醇与芳基或烯基锌试剂的交叉偶联反应。
Nickel-Catalyzed Cross-Coupling of Allyl Alcohols with Aryl- or Alkenylzinc Reagents.
机构信息
CAS Key Laboratory of Soft Matter Chemistry and Department of Chemistry, University of Science and Technology of China , Hefei, Anhui 230026, P. R. China.
Collaborative Innovation Center of Chemical Science and Engineering (Tianjin) , Tianjin 300072, P. R. China.
出版信息
J Org Chem. 2017 May 5;82(9):4542-4549. doi: 10.1021/acs.joc.6b02564. Epub 2016 Nov 17.
Nickel-catalyzed cross-coupling of allyl alcohols with aryl- and alkenylzinc chlorides through C-O bond cleavage was performed. Reaction of (E)-3-phenylprop-2-en-1-ol and 1-aryl-prop-2-en-1-ols with aryl- or alkenylzinc chlorides gave linear cross-coupling products. Reaction of 1-phenyl- or 1-methyl-substituted (E)-3-phenylprop-2-en-1-ol with aryl- or alkenylzinc chlorides resulted in 3-aryl/alkenyl-substituted (E)-(prop-1-ene-1,3-diyl)dibenzenes or 3-aryl/alkenyl-substituted (E)-(but-1-enyl)benzene. Reaction of allyl alcohol with p-MeNCHZnCl resulted in a mixture of normal coupling product 4-allyl-N,N-dimethylaniline and its isomerized product N,N-dimethyl-4-(prop-1-en-1-yl)aniline.
镍催化的通过 C-O 键断裂的烯丙醇与芳基和烯基氯化锌的交叉偶联反应被进行。（E）-3-苯基丙烯-2-醇和 1-芳基-丙烯-2-醇与芳基或烯基氯化锌的反应得到线性交叉偶联产物。1-苯基或 1-甲基取代的（E）-3-苯基丙烯-2-醇与芳基或烯基氯化锌的反应导致 3-芳基/烯基取代的（E）-（丙烯-1,3-二基）二苯或 3-芳基/烯基取代的（E）-（丁-1-烯基）苯。烯丙醇与 p-MeNCHZnCl 的反应得到正常偶联产物 4-烯丙基-N,N-二甲基苯胺及其异构化产物 N,N-二甲基-4-（丙烯-1-基）苯胺的混合物。
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