Recyclable and Reusable [RuCl2(p-cymene)]2/Cu(OAc)2/PEG-400/H2O System for Oxidative C-H Bond Alkenylations: Green Synthesis of Phthalides

被引：66

作者：

Zhao, Hong ^{[1
,2
,3
]}

Zhang, Tinli ^{[1
,2
]}

Yan, Tao ^{[1
,2
]}

Cai, Mingzhong ^{[1
,2
]}

机构：

[1] Jiangxi Normal Univ, Key Lab Funct Small Organ Mol, Minist Educ, Nanchang 330022, Peoples R China

[2] Jiangxi Normal Univ, Coll Chem & Chem Engn, Nanchang 330022, Peoples R China

[3] Guangdong Pharmaceut Univ, Sch Chem & Chem Engn, Guangzhou 510006, Guangdong, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 80卷 / 17期

基金：

中国国家自然科学基金;

关键词：

CROSS-COUPLING REACTIONS; INTRAMOLECULAR KETONE HYDROACYLATION; TEMPERATURE IONIC LIQUIDS; POLY(ETHYLENE GLYCOL); ORGANIC-SYNTHESIS; HECK REACTION; THALLATION-CARBONYLATION; PALLADIUM NANOPARTICLES; HOMOGENEOUS CATALYSIS; BENZOIC-ACIDS;

D O I：

10.1021/acs.joc.5b01388

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[RuCl2(p-cymene)](2) in a mixture of poly(ethylene glycol) (PEG-400) and water is shown to be an extremely efficient catalyst for the cross-dehydrogenative C-H bond alkenylation reaction between benzoic acids and alkenes. The reaction could be conducted at 80 degrees C using Cu(OAc)(2). H2O as oxidant, yielding a variety of phthalide derivatives in good to excellent yields. More importantly, both [RuCl2(p-cymene)](2) and Cu(OAc)(2) in the PEG-400/H2O system could be easily recycled and reused six times without any loss of catalytic activity.

引用

页码：8849 / 8855

页数：7

共 50 条

[1] Recyclable [Ru2Cl3(p-cymene)2][PF6]/Cu(OAc)2/PEG-400/H2O system for oxidative annulation of alkynes by aniline derivatives: Green synthesis of indoles
Liao, Yang
Wei, Ting
Yan, Tao
Cai, Mingzhong
[J]. TETRAHEDRON, 2017, 73 (09) : 1238 - 1246
[2] Recyclable [RuCl2(p-cymene)]2/PEG-400/H2O System for Efficient Annulation of N-Methoxybenzamides with Alkynes Under External Oxidant-Free Conditions
Jianying Li
Rong Liu
Qian Ye
Mingzhong Cai
[J]. Catalysis Letters, 2023, 153 : 732 - 739
[3] Recyclable and Reusable Pd(OAc)2/XPhos–SO3Na/PEG-400/H2O System for Cyanation of Aryl Chlorides with Potassium Ferrocyanide
Mingzhong Cai
Rong Liu
Caifeng Xu
Bin Huang
[J]. Catalysis Letters, 2022, 152 : 2688 - 2694
[4] Recyclable [RuCI2(p-cymene)]2/PEG-400/H2O System for Efficient Annulation of N-Methoxybenzamides with Alkynes Under External Oxidant-Free Conditions
Li, Jianying
Liu, Rong
Ye, Qian
Cai, Mingzhong
[J]. CATALYSIS LETTERS, 2023, 153 (03) : 732 - 739
[5] Recyclable and Reusable Pd(OAc)2/XPhos-SO3Na/PEG-400/H2O System for Cyanation of Aryl Chlorides with Potassium Ferrocyanide
Cai, Mingzhong
Liu, Rong
Xu, Caifeng
Huang, Bin
[J]. CATALYSIS LETTERS, 2022, 152 (09) : 2688 - 2694
[6] Recyclable and reusable PdCl2(PPh3)2/PEG-400/H2O system for the hydrophenylation of alkynes with sodium tetraphenylborate
Liu, Rong
Zhang, Tingli
Huang, Bin
Cai, Mingzhong
[J]. JOURNAL OF CHEMICAL RESEARCH, 2021, 45 (1-2) : 172 - 178
[7] [RuCl2(p-cymene)2]2 catalyzed cross dehydrogenative coupling (CDC) toward xanthone and fluorenone analogs through intramolecular C-H bond functionalization reaction
Manna, Sudipta Kumar
Manda, Srinivas Lavanya Kumar
Panda, Gautam
[J]. TETRAHEDRON LETTERS, 2014, 55 (42) : 5759 - 5763
[8] Recyclable and reusable NiCl2(PPh3)2/CuI/PEG-400/H2O system for the sonogashira coupling reaction of aryl iodides with alkynes
Wei, Ting
Zhang, Tingli
Huang, Bin
Tuo, Yuxin
Cai, Mingzhong
[J]. APPLIED ORGANOMETALLIC CHEMISTRY, 2015, 29 (12) : 846 - 849
[9] PEG-400-H2O as a green and recyclable medium for asymmetric hydrogenations of aromatic ketones catalyzed by RuCl2(TPPTS)2-(S,S)-DPENDS
Qin, Ruixiang
Wang, Jinbo
Xiong, Wei
Chen, Hua
Feng, Jian
Liu, Derong
[J]. TETRAHEDRON-ASYMMETRY, 2012, 23 (11-12) : 834 - 837
[10] Mechanistic Study of Acetate-Assisted C-H Activation of 2-Substituted Pyridines with [MCl2CP*]2 (M = Rh, Ir) and [RuCl2(p-cymene)]2
Boutadla, Youcef
Al-Duaij, Omar
Davies, David L.
Griffith, Gerald A.
Singh, Kuldip
[J]. ORGANOMETALLICS, 2009, 28 (02) : 433 - 440

← 1 2 3 4 5 →