13365-63-4Relevant articles and documents
Pd-Catalyzed Suzuki–Miyaura Cross-Coupling of Arylboronic Acids and α-Iminonitriles through C–CN Bond Activation
Liu, Kui,Tao, Shou-Wei,Qian, Chun,Zhu, Yong-Ming
supporting information, p. 4769 - 4775 (2018/09/06)
A Pd-catalyzed Suzuki–Miyaura cross-coupling reaction between arylboronic acids and α-iminonitriles has been developed. The reaction proceeds through selective activation of the C–CN bond, tolerates a wide range of substituents, and delivers the versatile ketone products in moderate to excellent yields.
Ligand-free Pd-catalyzed carbonylative cross-coupling reactions under atmospheric pressure of carbon monoxide: Synthesis of aryl ketones and heteroaromatic ketones
Li, Hongling,Yang, Min,Qi, Yanxing,Xue, Jijun
supporting information; experimental part, p. 2662 - 2667 (2011/06/25)
The carbonylative Suzuki cross-coupling reactions of boronic acids with aryl iodides catalyzed by Pd2(dba)3 as a ligand-free catalyst under atmospheric pressure of carbon monoxide has been firstly developed. Under mild reaction conditions, a broad range of aryl/heteroaryl iodides and aryl/heteroaryl boronic acids were selectively coupled to afford the corresponding diaryl ketones in good to excellent yields at low catalyst loadings (0.05 to 2 mol-%). Moreover, the catalyst can also be recycled. The carbonylative Suzuki cross-coupling reactions of boronic acids with aryl iodides catalyzed by Pd2(dba)3 as a ligand-free catalyst under an atmosphere of carbon monoxide has been developed. A broad range of aryl/heteroaryl iodides and aryl/heteroaryl boronic acids were selectively coupled to afford the corresponding diaryl ketones in good to excellent yields. The catalyst can also be recycled.
Deprotonative metalation of functionalized aromatics using mixed lithium-cadmium, lithium-indium, and lithium-zinc species
Snegaroff, Katia,L'Helgoual'ch, Jean-Martial,Bentabed-Ababsa, Ghenia,Nguyen, Tan Tai,Chevallier, Floris,Yonehara, Mitsuhiro,Uchiyama, Masanobu,Derdour, Aicha,Mongin, Florence
experimental part, p. 10280 - 10290 (2010/04/24)
In situ mixtures of CdCl2TMEDA (0.5 equiv; TMEDA = N,N,N',N'-tetramethylethylenediamine) or InCl3 (0.33 equiv) with [Li(tmp)] (tmp = 2,2,6,6-tetramethylpiperidino; 1.5 or 1.3 equiv, respectively) were compared with the previously described mixture of ZnCl2-TMEDA (0.5 equiv) and [Li(tmp)] (1.5 equiv) for their ability to deprotonate anisole, benzothiazole, and pyrimidine. [(tmp)3CdLi] proved to be the best base when used in tetrahydrofuran at room temperature, as demonstrated by subsequent trapping with iodine. The Cd-Li base then proved suitable for the metalation of a large range of aromatics including benzenes bearing reactive functional groups (CONEt2, CO2Me, CN, COPh) or heavy halogens (Br, I), and heterocycles (from the furan, thiophene, pyrrole, oxazole, thiazole, pyridine, and diazine series). Fivemembered heterocycles benefiting from doubly activated positions were similarly dideprotonated at room temperature. The aromatic lithium cadmates thus obtained were involved in palladium-catalyzed cross-coupling reactions or simply quenched with acid chlorides.