426265-40-9Relevant academic research and scientific papers
Palladium-catalyzed amination of aryl and heteroaryl tosylates at room temperature
Ogata, Tokutaro,Hartwig, John F.
, p. 13848 - 13849 (2008)
Mild palladium-catalyzed aminations of aryl tosylates and the first aminations of heteroaryl tosylates are described. In the presence of the combination of L2Pd(0) (L = P(o-tol)3) and the hindered Josiphos ligand CyPF-t-Bu, a variety of primary alkylamines and arylamines react with both aryl and heteroaryl tosylates at room temperature to form the corresponding secondary arylamines in high yields with complete selectivity for the monoarylamine. These reactions at room temperature occur in many cases with catalyst loadings of 0.1 mol % and 0.01 mol % in one case, constituting the most efficient aminations of aryl tosylates by nearly 2 orders of magnitude. This catalyst is made practical by the development of a convenient method to synthesize the L2Pd(0) precursor. This complex is stable to air as a solid. In contrast to conventional relative rates for reactions of aryl sulfonates, the reactions of aryl tosylates are faster than parallel reactions of aryl triflates, and the reactions of aryl tosylates are faster than parallel or competitive reactions of aryl chlorides. Copyright
Suzuki-Miyaura coupling of aryl sulfonates with arylboronic acids using a morpholine-Pd(OAc)2 catalyst system
Abe, Taichi,Mino, Takashi,Watanabe, Kohei,Yagishita, Fumitoshi,Sakamoto, Masami
, p. 3909 - 3916 (2014/06/24)
We report a new catalyst system, a morpholine-Pd(OAc)2 complex, for Suzuki-Miyaura coupling of aryl tosylates or mesylates with arylboronic acids to give biaryl compounds. The morpholine-Pd(OAc)2 catalyst system is proposed to be a precursor of the catalytically active species in the coupling reaction. Aryl chlorides and aryl triflates can also be used in this coupling reaction. Altogether, 22 biaryl compounds were obtained using this catalyst system. We report a new catalyst system, a morpholine-Pd(OAc) 2 complex, for Suzuki-Miyaura coupling of aryl tosylates or mesylates with arylboronic acids to give biaryl compounds. The morpholine-Pd(OAc) 2 catalyst system is proposed to be a precursor of the catalytically active species in the coupling reaction. Copyright
One-pot primary aminomethylation of aryl and heteroaryl halides with sodium phthalimidomethyltrifluoroborate
Murai, Norio,Miyano, Masayuki,Yonaga, Masahiro,Tanaka, Keigo
supporting information; experimental part, p. 2818 - 2821 (2012/07/17)
A one-pot primary aminomethylation of aryl halides, triflates, mesylates, and tosylates via Suzuki-Miyaura cross-coupling reactions with sodium phthalimidomethyltrifluoroborate followed by deamidation with ethylenediamine is reported.
Palladium-catalyzed borylation of aryl mesylates and tosylates and their applications in one-pot sequential suzuki-miyaura biaryl synthesis
Chow, Wing Kin,So, Chau Ming,Lau, Chak Po,Kwong, Fuk Yee
supporting information; experimental part, p. 6913 - 6917 (2011/08/03)
Top of the one-pots! The first palladium-catalyzed borylation of aryl tosylates and mesylates is described. The reaction conditions are mild and provide excellent functional-group compatibility (e.g., R=CN, CHO, COOMe, C(O)R, NH2, or NH-indole; see scheme). Pd/MeO-CM-phos allows one-pot sequential reactions in the preparation of unsymmetrical biaryls. Copyright
Suzuki-Miyaura coupling of aryl tosylates catalyzed by an array of indolyl phosphine-palladium catalysts
So, Chau Ming,Lau, Chak Po,Chan, Albert S. C.,Kwong, Fuk Yee
, p. 7731 - 7734 (2008/12/22)
A family of indolyl phosphine ligands was applied to Suzuki-Miyaura cross-coupling of aryl tosylates. Catalyst loading can be reduced to 0.2 mol % for coupling of nonactivated aryl tosylate. A challenging example for room temperature coupling is realized. The scope of this highly active Pd/L2 system can be extended to other boron nucleophiles, including trifluoroborate salts and boronate esters. The ligand structural comparisons toward the reactivity in tosylate couplings are also described.
The first general palladium catalyst for the Suzuki-Miyaura and carbonyl enolate coupling of aryl arenesulfonates
Nguyen, Hanh Nho,Huang, Xiaohua,Buchwald, Stephen L.
, p. 11818 - 11819 (2007/10/03)
The first general method for the palladium-catalyzed Suzuki-Miyaura and carbonyl enolate coupling of unactivated aryl arenesulfonates was developed utilizing XPhos, 1, and Pd(OAc)2. This is of significant interest because aryl tosylates and aryl benzenesulfonates are more easily handled and considerably less expensive than aryl triflates. This catalyst system effects the coupling of a variety of aryl, heteroaryl, and extremely hindered arylboronic acids with different aryl tosylates, under mild conditions. The same catalyst was employed in the first carbonyl enolate coupling of aryl arensulfonates. Copyright
