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基于氯化胆碱的低共熔体系在甲基酮的连续Friedländer反应及钯催化sp C-H官能化反应中的应用

Choline Chloride-Based Deep Eutectic Systems in Sequential Friedländer Reaction and Palladium-Catalyzed sp CH Functionalization of Methyl Ketones.

作者信息

Teja Chitrala, Nawaz Khan Fazlur Rahman

机构信息

Organic and Medicinal Chemistry Research Laboratory, School of Advanced Sciences, Vellore Institute of Technology, Vellore 632 014, Tamil Nadu, India.

出版信息

ACS Omega. 2019 May 2;4(5):8046-8055. doi: 10.1021/acsomega.9b00310. eCollection 2019 May 31.

DOI:10.1021/acsomega.9b00310
PMID:31459894
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6648676/
Abstract

A volatile organic solvent-free and choline chloride (ChCl)-based deep eutectic system (DES)-mediated sp-CH functionalization of acetophenones with benzyl alcohols to the corresponding α, β-saturated ketones is accounted for. The domino dehydrogenation-aldol condensation (hydrogenation borrowing concept) has been successfully attempted with palladium-tetrakis(triphenylphosphine) [Pd(PPh)] catalyst-xantphos ligand combination. Furthermore, a sequential Friedländer reaction of 2-aminobenzophenone and palladium-catalyzed α-alkylation of the quinolinyl methyl ketone with benzyl alcohols in ChCl-based DES have been successfully investigated. The C-C bond formation through sp-CH functionalization involves a wide scope of the substrates, high atom efficiency, chemoselectivity, and environmentally friendly strategy.

摘要

报道了一种无挥发性有机溶剂且基于氯化胆碱（ChCl）的低共熔体系（DES）介导的苯乙酮与苯甲醇的sp-CH官能化反应，生成相应的α,β-不饱和酮。使用钯-四（三苯基膦）[Pd(PPh)]催化剂-联二萘酚配体组合成功尝试了多米诺脱氢-羟醛缩合反应（借氢概念）。此外，还成功研究了2-氨基二苯甲酮在基于ChCl的DES中的连续Friedländer反应以及喹啉基甲基酮与苯甲醇的钯催化α-烷基化反应。通过sp-CH官能化形成C-C键涉及广泛的底物范围、高原子效率、化学选择性以及环境友好策略。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8e70/6648676/c2c43cae98c9/ao-2019-00310a_0007.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8e70/6648676/c2c43cae98c9/ao-2019-00310a_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8e70/6648676/9c783b4d3167/ao-2019-00310a_0003.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8e70/6648676/c2c43cae98c9/ao-2019-00310a_0007.jpg

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