115933-15-8Relevant articles and documents
Palladium-catalyzed cross-coupling of five-membered heterocyclic silanolates
Denmark, Scott E.,Baird, John D.,Regens, Christopher S.
, p. 1440 - 1455 (2008)
(Chemical Equation Presented) The preparation of π-rich 2-aryl heterocycles by palladium-catalyzed cross-coupling of sodium heteroarylsilanolates with aryl iodides, bromides, and chlorides is described. The cross-coupling process was developed through extensive optimization of the following key variables: (1) identification of stable, isolable alkali metal silanolates, (2) identification of conditions for preformation and isolation of silanolate salts, (3) judicious choice in the palladium catalyst/ligand combination, and (4) selection of the protecting group on the nitrogen of indole. It was found that the alkali metal silanolates, either isolated or formed in situ, offered a significant rate enhancement and broader substrate scope over the use of silanols activated by Bronsted bases such as NaOt-Bu. In addition, the optimized conditions for the cross-coupling of 2-indolylsilanolates were readily applied to the cross-coupling of 2-pyrrolyl-, 2-furyl-, and 2-thienylsilanolates.
Nickel-catalyzed cross-coupling of arene-or heteroarenecarbonitriles with aryl-or heteroarylmanganese reagents through C-CN bond activation
Liu, Ning,Wang, Zhong-Xia
, p. 1641 - 1645 (2012)
The nickel-catalyzed cross-coupling reaction of arene- or heteroarenecarbonitriles with aryl- or heteroarylmanganese reagents via C-CN bond activation has been developed. Both electron-rich and electron-deficient nitriles can be employed as the electrophilic substrates. The reaction tolerates a range of functional groups and aromatic heterocycles. Copyright
Catalytic direct cross-coupling of organolithium compounds with aryl chlorides
Hornillos, Valentin,Giannerini, Massimo,Vila, Carlos,Fananas-Mastral, Martin,Feringa, Ben L.
, p. 5114 - 5117 (2013)
Palladium-catalyzed direct cross-coupling of aryl chlorides with a wide range of (hetero)aryl lithium compounds is reported. The use of Pd-PEPPSI-IPent or Pd2(dba)3/XPhos as the catalyst allows for the preparation of biaryl and heterobiaryl compounds in high yields under mild conditions (room temperature to 40 C) with short reaction times.
One-Pot Dual Catalysis of a Photoactive Coordination Polymer and Palladium Acetate for the Highly Efficient Cross-Coupling Reaction via Interfacial Electron Transfer
Guo, Zhifen,Liu, Xin,Che, Yan,Chen, Dashu,Xing, Hongzhu
supporting information, p. 2695 - 2705 (2022/02/14)
We report herein an exploration of the straightforward one-pot dual-catalysis strategy, i.e., direct combination of a photoactive coordination polymer (CP) with another metal catalyst, for carrying out the desirable photoinduced organic transformation. Th
Potassium trimethylsilanolate enables rapid, homogeneous suzuki-miyaura cross-coupling of boronic esters
Delaney, Connor P.,Kassel, Vincent M.,Denmark, Scott E.
, p. 73 - 80 (2019/12/24)
Herein, a mild and operationally simple method for the Suzuki-Miyaura cross-coupling of boronic esters is described. Central to this advance is the use of the organic-soluble base, potassium trimethylsilanolate, which allows for a homogeneous, anhydrous cross-coupling. The coupling proceeds at a rapid rate, often furnishing products in quantitative yield in less than 5 min. By applying this method, a >10-fold decrease in reaction time was observed for three published reactions which required >48 h to reach satisfactory conversion.
Metal-Free Aerobic Oxidative Selective C-C Bond Cleavage in Heteroaryl-Containing Primary and Secondary Alcohols
Xia, Anjie,Qi, Xueyu,Mao, Xin,Wu, Xiaoai,Yang, Xin,Zhang, Rong,Xiang, Zhiyu,Lian, Zhong,Chen, Yingchun,Yang, Shengyong
supporting information, (2019/05/07)
A transition-metal-free aerobic oxidative selective C-C bond-cleavage reaction in primary and secondary heteroaryl alcohols is reported. This reaction was highly efficient and tolerated various heteroaryl alcohols, generating a carboxylic acid derivative and a neutral heteroaromatic compound. Experimental studies combined with density functional theory calculations revealed the mechanism underlying the selective C-C bond cleavage. This strategy also provides an alternative simple approach to carboxylation reaction.
