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首页> 外文期刊>Dalton transactions: An international journal of inorganic chemistry >Hydroamination of diphenylbutadiyne with secondary N-methyl-anilines using the dipotassium tetrakis(2,6-diisopropylanilino)calciate precatalyst
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Hydroamination of diphenylbutadiyne with secondary N-methyl-anilines using the dipotassium tetrakis(2,6-diisopropylanilino)calciate precatalyst

机译：使用四（2,6-二异丙基苯胺基）钙二钾预催化剂用仲N-甲基苯胺加氢二苯基丁二炔

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摘要

The approved precatalyst [K2Ca{N(H)Dipp}(4)] was employed to study the hydroamination of diphenylbutadiyne with N-methyl-anilines in tetrahydrofuran at room temperature. The hydroamination occurs regioselectively within a few hours yielding (N-methyl)-(N-aryl)-1,4-diphenylbut-1-ene-3-yne-1-ylamine with phenyl (1a), 4-tolyl (1b) and 4-fluorophenyl groups (1c). In all cases a mixture of E-and Z-isomers is obtained. The second hydroamination step requires drastically extended reaction times and is successful only for the reaction of diphenylbutadiyne with N-methyl-aniline and N-methyl-4-fluoroaniline giving 1,4-diphenyl-1,4-bis(N-methyl-anilino)buta-1,3-diene [R = H (2a) and F (2c)]; a mixture of E,E-, E,Z- and Z,Z-isomers is obtained. The X-ray structures of E-1a, E-1b and E-1c show a slightly shortened N-C bond to the alkene moieties. Due to enhanced steric strain the anilino units of Z,Z-2c and Z,Z-3 turn away from the butadiene unit and consequently, the lone pair at the planar nitrogen atoms slightly interacts with the adjacent aryl groups.
机译：批准的预催化剂[K2Ca {N（H）Dipp}（4）]用于研究在室温下四氢呋喃中二苯基丁二炔与N-甲基苯胺的加氢胺化作用。加氢胺化在几个小时内区域选择性地发生，生成带有苯基（1a），4-甲苯基（1b）的（N-甲基）-（N-芳基）-1,4-二苯基丁-1-烯-3-炔-1-基胺和4-氟苯基（1c）。在所有情况下，都会得到E和Z异构体的混合物。第二个加氢胺化步骤需要大大延长反应时间，并且仅对二苯基丁二炔与N-甲基苯胺和N-甲基-4-氟苯胺的反应成功，从而得到1,4-二苯基-1,4-双（N-甲基-苯胺基） ）buta-1,3-diene [R = H（2a）and F（2c）];得到E，E-，E，Z-和Z，Z-异构体的混合物。 E-1a，E-1b和E-1c的X射线结构显示与烯烃部分的N-C键略微缩短。由于增加的空间应变，Z，Z-2c和Z，Z-3的苯胺单元远离丁二烯单元，因此，平面氮原子上的孤对与相邻的芳基略有相互作用。

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