Highly active catalyst for the heterogeneous Suzuki-Miyaura reaction: assembled complex of palladium and non-cross-linked amphiphilic polymer.

Highly active catalyst for the heterogeneous Suzuki-Miyaura reaction: assembled complex of palladium and non-cross-linked amphiphilic polymer.
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DOI:
10.1021/jo034354v
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发表时间:
2003-09
期刊:
The Journal of organic chemistry
影响因子:
--
通讯作者:
Yoichi M. A. Yamada;K. Takeda;Hideyo Takahashi;S. Ikegami
Yoichi M. A. Yamada;K. Takeda;Hideyo Takahashi;S. Ikegami
中科院分区:
其他
文献类型:
--
作者:
Yoichi M. A. Yamada;K. Takeda;Hideyo Takahashi;S. Ikegami

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以Pd(NH_4)_2PdCl_4(1))和非交联两亲性共聚物聚(N-异丙基丙烯酰胺-co-4-二苯基苯乙烯基膦)(2)为原料,制备了一种组装型不溶性催化剂PdAS。发现PdAS是Suzuki-Miyaura反应的优良催化剂,有三点:(1)使用8 × 10 ~(-7)~ 5 × 10 ~(-4)mol当量的PdAS,经过简单的后处理,可有效地得到偶联产物,转化数高达1,250,000。(2)该催化剂可重复使用多次而不损失催化活性。(3)PdAS在任何反应介质(即,水或含水或无水有机溶剂)。PdAS的分析研究表明,2中的膦配位钯形成PdCl 2(PPh 2Ar)2物种。
An assembled insoluble catalyst, PdAS, prepared from palladium ((NH4)2PdCl4 (1)) and non-cross-linked amphiphilic copolymer poly(N-isopropylacrylamide-co-4-diphenylstyrylphosphine) (2) was developed. It was found that PdAS is an excellent catalyst for the Suzuki-Miyaura reaction on three points: (1) The use of 8 x 10(-7) to 5 x 10(-4) mol equiv of PdAS afforded the coupling products efficiently after easy workup, with the turnover number reaching up to 1,250,000. (2) The catalyst was reusable many times without loss of catalytic activity. (3) PdAS showed good stability in any reaction medium (i.e., water or aqueous or anhydrous organic solvents). Analytical study of PdAS indicates that the phosphines in 2 coordinate to palladium to form PdCl2(PPh2Ar)2 species.