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首页> 外文期刊>Dalton transactions: An international journal of inorganic chemistry >A protic ionic liquid as an atom economical solution for palladium catalyzed asymmetric allylic alkylation
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A protic ionic liquid as an atom economical solution for palladium catalyzed asymmetric allylic alkylation

机译：一种质子离子液体作为钯催化不对称烯丙基烷基化的原子经济溶液

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摘要

The asymmetric allylic alkylation of rac-1,3-diphenyl-3-acetoxyprop-1-ene (I) catalysed by palladium and diverse phosphorus containing ligands [(S)-BINAP, (R,R)-Chiraphite and (R,R)-Et-Duphos] in an ionic liquid [HDBU][OAc] was successfully performed, achieving full conversions and up to 96% ee of the (S)-product when (R,R)-Et-Duphos was used as a ligand. The reaction could be performed using an equimolar amount of substrate, malonate and base DBU, in which case the total products sum to the desired alkylated product and the ionic pair [HDBU][OAc]; this system thus produces its own IL solvent as the only co-product. These catalytic systems were active in recycling experiments for up to four cycles, albeit with a loss of activity due to the poor retention of palladium in the ionic liquid. The catalytic performance of each Pd/ligand system was optimized by varying the ratio of the substrate and malonate. Systems based on [HDBU][OAc] were found to be the best.
机译：钯和含有配体的不同磷催化的RAC-1,3-二苯基-3-乙酰氧基丙烯酸-1-烯丙基烷基（I）的不对称烯丙基烷基化[（s）-binap，（r，r）和（r，r ）在离子液体[HDBU] [HDBU] [HDBU] [HDBU] [HDBU] [HDBU] [HDBU] [HDBU] [HDBU]中进行全转化，当使用（R）-et-Duphos作为a时，达到全面的转化率和高达96％的EE - Δtoduct 配体。 反应可以使用等摩尔量的底物，丙二酸酯和基础DBU进行，在这种情况下，总产物总和至所需的烷基化产物和离子对[HDBU] [OAC]; 因此，该系统产生自己的IL溶剂作为唯一的共同产品。 这些催化系统在再循环实验中，最多四个循环，尽管在离子液体中的钯保持不变导致的活性丧失。 通过改变基材和丙酮酸的比例来优化每个Pd /配体系的催化性能。 发现基于[HDBU] [OAC]的系统是最好的。

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