Ligand-Enabled Gold-Catalyzed C(sp2)-O Cross-Coupling Reactions

被引：42
作者：
Das, Avishek [1 ]
Patil, Nitin T. [1 ]
机构：
[1] Indian Inst Sci Educ & Res Bhopal, Dept Chem, Bhopal 462066, India
来源：
ACS CATALYSIS | 2023年 / 13卷 / 06期
关键词：
gold catalysis; oxidative addition; reductive elimination; C-O cross-coupling; methoxylation; aryl alkyl ethers; O BOND FORMATION; ACTIVATED ARYL; BROMIDES; HALIDES; ETHYNYLBENZIODOXOLONES; HYDROXYLATION; REACTIVITY; COMPLEXES; CHEMISTRY; IODIDES;
D O I：
10.1021/acscatal.3c00338
中图分类号：
O64 [物理化学（理论化学）、化学物理学];
学科分类号：
070304 ; 081704 ;
摘要：
Reported herein is a ligand-enabled gold-catalyzed C(sp2)-O cross-coupling reaction of aryl iodides and aliphatic alcohols. The synthesis of a variety of aryl alkyl ethers including complex biomolecules and various medicinally relevant motifs has been achieved to demonstrate the usefulness of the method. The importance of gold catalysis has been highlighted by overcoming the selectivity issues that are in general observed for C-O cross -coupling reactions when other transition metals are used as catalysts. + R -OH R = alkyl ./ 63 examples OR Au iota CI* 4,/ 50 -99% yields o Directing group free o Mild reaction conditions 0 Electron-poor Ad preferred over electron-rich An N III NMe2 PAd2
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页码：3847 / 3853
页数：7
相关论文
共 78 条
[1]   Alkyl Enol Ethers: Development in Intermolecular Organic Transformation [J].
Ahmad, Sarwat Asma Ziya ;
Jena, Tapan Kumar ;
Khan, Faiz Ahmed .
CHEMISTRY-AN ASIAN JOURNAL, 2021, 16 (13) :1685-1702
[2]   Ligand-Enabled Gold-Catalyzed C(sp2)-N Cross-Coupling Reactions of Aryl Iodides with Amines [J].
Akram, Manjur O. ;
Das, Avishek ;
Chakrabarty, Indradweep ;
Patil, Nitin T. .
ORGANIC LETTERS, 2019, 21 (19) :8101-8105
[3]   Oxidant-free oxidative gold catalysis: the new paradigm in cross-coupling reactions [J].
Akram, Manjur O. ;
Banerjee, Somsuvra ;
Saswade, Sagar S. ;
Bedi, Vaibhav ;
Patil, Nitin T. .
CHEMICAL COMMUNICATIONS, 2018, 54 (79) :11069-11083
[4]   Cross-Coupling Reactions of Aryldiazonium Salts with Allylsilanes under Merged Gold/Visible-Light Photoredox Catalysis [J].
Akram, Manjur O. ;
Mali, Pramod S. ;
Patil, Nitin T. .
ORGANIC LETTERS, 2017, 19 (12) :3075-3078
[5]   A facile strategy for accessing 3-alkynylchromones through gold-catalyzed alkynylation/cyclization of o-hydroxyarylenaminones [J].
Akram, Manjur O. ;
Bera, Saibal ;
Patil, Nitin T. .
CHEMICAL COMMUNICATIONS, 2016, 52 (83) :12306-12309
[6]   An improved cu-based catalyst system for the reactions of alcohols with aryl halides [J].
Altman, Ryan A. ;
Shafir, Alexandr ;
Choi, Alice ;
Lichtor, Phillip A. ;
Buchwald, Stephen L. .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (01) :284-286
[7]   Gold-Catalyzed Alkynylative Meyer-Schuster Rearrangement [J].
Banerjee, Somsuvra ;
Ambegave, Shivhar B. ;
Mule, Ravindra D. ;
Senthilkumar, Beeran ;
Patil, Nitin T. .
ORGANIC LETTERS, 2020, 22 (12) :4792-4796
[8]   Gold and hypervalent iodine(iii): liaisons over a decade for electrophilic functional group transfer reactions [J].
Banerjee, Somsuvra ;
Bhoyare, Vivek W. ;
Patil, Nitin T. .
CHEMICAL COMMUNICATIONS, 2020, 56 (18) :2677-2690
[9]   Gold-Catalyzed 1,2-Oxyalkynylation of N-Allenamides with Ethylnylbenziodoxolones [J].
Banerjee, Somsuvra ;
Senthilkumar, Beeran ;
Patil, Nitin T. .
ORGANIC LETTERS, 2019, 21 (01) :180-184
[10]   Exploiting the dual role of ethynylbenziodoxolones in gold-catalyzed C(sp)-C(sp) cross-coupling reactions [J].
Banerjee, Somsuvra ;
Patil, Nitin T. .
CHEMICAL COMMUNICATIONS, 2017, 53 (56) :7937-7940
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