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聚乙烯亚胺改性聚合物作为一种高效的钯清除剂和功能性非均相钯催化剂的有效催化剂载体。

Polyethyleneimine-Modified Polymer as an Efficient Palladium Scavenger and Effective Catalyst Support for a Functional Heterogeneous Palladium Catalyst.

作者信息

Yamada Tsuyoshi, Kobayashi Yutaka, Ito Naoya, Ichikawa Tomohiro, Park Kwihwan, Kunishima Kouki, Ueda Shun, Mizuno Masahiro, Adachi Tadashi, Sawama Yoshinari, Monguchi Yasunari, Sajiki Hironao

机构信息

Laboratory of Organic Chemistry, Gifu Pharmaceutical University, 1-25-4 Daigaku-nishi, Gifu 501-1196, Japan.

Separation Materials Group, Functional Organic Materials Laboratory, Fukuoka R&D Center, Mitsubishi Chemical Corporation, 1-1 Kurosaki-Shiroishi, Yahatanishi-ku, Kitakyushu-shi, Fukuoka 806-0004, Japan.

出版信息

ACS Omega. 2019 Jun 13;4(6):10243-10251. doi: 10.1021/acsomega.9b00707. eCollection 2019 Jun 30.

DOI:10.1021/acsomega.9b00707
PMID:31460116
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6649293/
Abstract

The polyethyleneimine-modified polymers, polystyrene-divinylbenzene-based (TAs) and polymethacrylate-based polymers (TAm), were used as palladium scavengers to eliminate residual palladium species after palladium on carbon-catalyzed Sonogashira-type coupling reaction. Since both TAs and TAm indicated relatively favorable elimination abilities toward residual palladium species in the reaction mixture, the affinities of TAs and TAm for palladium species were used as supports for palladium catalysts. The TAm-supported palladium catalyst (Pd/TAm) indicated better catalyst properties for the chemoselective hydrogenation compared to those of the corresponding TAs-supported palladium catalyst (Pd/TAs). Aromatic benzyl ethers; aromatic and aliphatic -Cbzs; and aromatic carbonyl groups were smoothly hydrogenated in the presence of 1-5 mol % of Pd/TAm in MeOH or 2-PrOH. In contrast, the hydrogenation of aromatic ketones was selectively suppressed in morpholine which act as appropriate catalyst poison and solvent. Furthermore, Pd/TAm-catalyzed chemoselective hydrogenation was applicable to continuous-flow reaction.

摘要

聚乙烯亚胺改性的聚合物，聚苯乙烯 - 二乙烯基苯类（TAs）和聚甲基丙烯酸酯类聚合物（TAm），被用作钯清除剂，以在碳载钯催化的Sonogashira型偶联反应后消除残留的钯物种。由于TAs和TAm对反应混合物中的残留钯物种均表现出相对良好的清除能力，因此TAs和TAm对钯物种的亲和力被用作钯催化剂的载体。与相应的TAs负载钯催化剂（Pd/TAs）相比，TAm负载钯催化剂（Pd/TAm）在化学选择性氢化方面表现出更好的催化剂性能。在甲醇或2 - 丙醇中，1 - 5 mol%的Pd/TAm存在下，芳族苄基醚、芳族和脂肪族 - Cbzs以及芳族羰基能够顺利氢化。相比之下，在作为合适催化剂毒物和溶剂的吗啉中，芳族酮的氢化反应被选择性抑制。此外，Pd/TAm催化的化学选择性氢化适用于连续流动反应。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9eb6/6649293/3daa307c4f0c/ao-2019-00707x_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9eb6/6649293/3dc66ad19fac/ao-2019-00707x_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9eb6/6649293/433e12bdd883/ao-2019-00707x_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9eb6/6649293/2af4cac6decd/ao-2019-00707x_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9eb6/6649293/3daa307c4f0c/ao-2019-00707x_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9eb6/6649293/3dc66ad19fac/ao-2019-00707x_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9eb6/6649293/433e12bdd883/ao-2019-00707x_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9eb6/6649293/2af4cac6decd/ao-2019-00707x_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9eb6/6649293/3daa307c4f0c/ao-2019-00707x_0004.jpg

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