51241-33-9Relevant articles and documents
Oxalic Diamides and tert-Butoxide: Two Types of Ligands Enabling Practical Access to Alkyl Aryl Ethers via Cu-Catalyzed Coupling Reaction
Chen, Zhixiang,Jiang, Yongwen,Zhang, Li,Guo, Yinlong,Ma, Dawei
supporting information, p. 3541 - 3549 (2019/02/26)
A robust and practical protocol for preparing alkyl aryl ethers has been developed, which relies on using two types of ligands to promote Cu-catalyzed alkoxylation of (hetero)aryl halides. The reaction scope is very general for a variety of coupling partners, particularly for challenging secondary alcohols and (hetero)aryl chlorides. In case of coupling with aryl chlorides and bromides, two oxalic diamides serve as the powerful ligands. The tert-butoxide is first demonstrated as a ligand for Cu-catalyzed coupling reaction, leading to alkoxylation of aryl iodides complete at room temperature. Additionally, a number of carbohydrate derivatives are applicable for this coupling reaction, affording the corresponding carbohydrate-aryl ethers in 29-98% yields.
A single phosphine ligand allows palladium-catalyzed intermolecular C-O bond formation with secondary and primary alcohols
Wu, Xiaoxing,Fors, Brett P.,Buchwald, Stephen L.
supporting information; experimental part, p. 9943 - 9947 (2011/12/05)
Forging a bond: An efficient, general palladium catalyst for C-O bond-forming reactions of secondary and primary alcohols with a range of aryl halides has been developed using the ligand 1. Heteroaryl halides, and for the first time, electron-rich aryl halides can be coupled with secondary alcohols. A diverse set of substrate combinations are possible with just a single ligand, thus obviating the need to survey multiple ligands. Copyright
Use of tunable ligands allows for intermolecular Pd-catalyzed C-O bond formation
Vorogushin, Andrei V.,Huang, Xiaohua,Buchwald, Stephen L.
, p. 8146 - 8149 (2007/10/03)
Bulky biaryl phosphine ligands facilitate Pd-catalyzed C-O coupling reactions of aryl halides with primary and secondary alcohols by promoting reductive elimination at the expense of β-hydride elimination. The key to their success is the ability to match the size of the ligand to that of the combination of substrates. The efficient coupling of a number of unactivated aryl chlorides and bromides with cyclic and acyclic secondary alcohols was achieved. This included the coupling of allylic alcohols for the first time in a Pd-catalyzed coupling process.