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Palladium-Catalyzed Insertion of Ethylene and 1,1-Disubstituted Difunctional Olefins: An Experimental and Computational Study.
ChemPlusChem ( IF 3.0 ) Pub Date : 2020-05-22 , DOI: 10.1002/cplu.202000309 Shahaji R Gaikwad 1, 2 , Ketan Patel 1, 3 , Satej S Deshmukh 1, 2 , Nilesh R Mote 1, 2 , Rajkumar S Birajdar 1, 2 , Satish P Pandole 4 , Jeetender Chugh 5 , Samir H Chikkali 1, 2
ChemPlusChem ( IF 3.0 ) Pub Date : 2020-05-22 , DOI: 10.1002/cplu.202000309 Shahaji R Gaikwad 1, 2 , Ketan Patel 1, 3 , Satej S Deshmukh 1, 2 , Nilesh R Mote 1, 2 , Rajkumar S Birajdar 1, 2 , Satish P Pandole 4 , Jeetender Chugh 5 , Samir H Chikkali 1, 2
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Insertion or coordination copolymerization of ethylene with di‐substituted olefins is challenging and the choice of di‐substituted mono‐functional olefin versus di‐substituted di‐functional olefin (DDO) appears to be decisive. Here we show that DDO‐inserted species are amenable to ethylene insertion and polymerization. DDOs such as 2‐acetamidoacrylic acid (AAA), methyl 2‐acetamidoacrylate (MAAA), and ethyl 2‐cyanoacrylate (ECA) were treated with palladium complex [{P∧O}PdMe(L)] (P∧O=κ2‐P,O−Ar2PC6H4SO2O with Ar=2‐MeOC6H4; L=C2H6OS) and the existence of respective insertion intermediates in moderate yield (up to 37 %) was established. These intermediates were exposed to ethylene and corresponding ethylene‐inserted products were isolated and characterized. A careful comparison with three model compounds confirmed ethylene insertion and polymerization. Thus, the combined experimental and computational investigations show that DDO‐inserted species can undergo ethylene insertion and polymerization.
中文翻译：
钯催化的乙烯和1,1-双取代双官能烯烃的插入：一项实验和计算研究。
乙烯与双取代烯烃的插入或配位共聚具有挑战性，选择双取代单官能烯烃与双取代双官能烯烃（DDO）似乎是决定性的。在这里，我们表明DDO插入的物种适合乙烯插入和聚合。DDOS如2- acetamidoacrylic酸（AAA），甲基2-乙酰氨基（MAAA），和2-氰基丙烯酸酯（ECA）用钯复合物处理[{P∧O} PDME（L）]（P∧O=κ 2 -P，O-Ar 2 PC 6 H 4 SO 2 O，Ar = 2-MeOC 6 H 4 ; L = C 2 H 6OS）和中等插入率（高达37％）的各个插入中间体的存在。这些中间体暴露于乙烯，并分离和表征了相应的乙烯插入产物。与三种模型化合物的仔细比较证实了乙烯的插入和聚合。因此，结合实验和计算研究表明，DDO插入的物质可能会发生乙烯插入和聚合反应。
更新日期：2020-06-25
中文翻译：
钯催化的乙烯和1,1-双取代双官能烯烃的插入：一项实验和计算研究。
乙烯与双取代烯烃的插入或配位共聚具有挑战性，选择双取代单官能烯烃与双取代双官能烯烃（DDO）似乎是决定性的。在这里，我们表明DDO插入的物种适合乙烯插入和聚合。DDOS如2- acetamidoacrylic酸（AAA），甲基2-乙酰氨基（MAAA），和2-氰基丙烯酸酯（ECA）用钯复合物处理[{P∧O} PDME（L）]（P∧O=κ 2 -P，O-Ar 2 PC 6 H 4 SO 2 O，Ar = 2-MeOC 6 H 4 ; L = C 2 H 6OS）和中等插入率（高达37％）的各个插入中间体的存在。这些中间体暴露于乙烯，并分离和表征了相应的乙烯插入产物。与三种模型化合物的仔细比较证实了乙烯的插入和聚合。因此，结合实验和计算研究表明，DDO插入的物质可能会发生乙烯插入和聚合反应。
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