21002-15-3Relevant academic research and scientific papers
Nickel-catalyzed Suzuki-Miyaura coupling of heteroaryl ethers with arylboronic acids
Li, Xiao-Jian,Zhang, Jin-Ling,Geng, Yu,Jin, Zhong
, p. 5078 - 5084 (2013/06/27)
Nickel-catalyzed Suzuki-Miyaura coupling of heteroaryl ethers with arylboronic acids was described. Selective activation of the phenol C-O bonds was achieved by converting them into the corresponding aryl 2,4-dimethoxy-1,3,5- triazine-6-yl ethers, in which aryl C-O bond could be selectively cleaved with inexpensive, air-stable NiCl2(dppf) as a catalyst. Coupling of these readily accessible heteroaryl ethers proved tolerant of extensive functional groups.
Stepwise versus concerted mechanisms at trigonal carbon: Transfer of the 1,3,5-triazinyl group between aryl oxide ions in aqueous solution
Renfrew, A. Hunter M.,Rettura, Donatella,Taylor, John A.,Whitmore, James M. J.,Williams, Andrew
, p. 5484 - 5491 (2007/10/02)
Displacements of 4-nitrophenolate ions from 2-(4-nitrophenoxy)-4,6-dimethoxy-1,3,5-triazine by substituted phenolate ions in aqueous solution obey a linear Br?nsted-type equation, log kArO = 0.951pKa - 10.98, over a range of pKa values greater than and less than the pKa of the leaving phenol. The absence of curvature is consistent with a mechanism involving a single transition state. This conclusion is supported by the existence of cross-correlation effects (Pxy = 0.0561) on βnuc of the pKa of the leaving group and on β1g of the pKa of the nucleophile on β1g. The value of βeq, the Br?nsted selectivity for transfer of the triazinyl function between phenolate ions, is calculated from the Br?nsted data to be 1.48. The identity reaction of 3,4-dinitrophenolate ion with the (3,4-dinitrophenoxy)triazine is calculated to have a Kreevoy-Albery τ value of 1.04, indicating that in this case changes in effective charge on entering and leaving ligands are approximately balanced.
A Single Transition State in Nucleophilic Aromatic Substitution: Reaction of Phenolate Ions with 2-(4-Nitrophenoxy)-4,6-dimethoxy-1,3,5-triazine in Aqueous Solution
Hunter, A.,Renfrew, M.,Taylor, John A.,Whitmore, James M. J.,Williams, Andrew
, p. 1703 - 1704 (2007/10/02)
The absence of curvature in the Broensted dependence for displacement of 4-nitrophenolate ion from the title ether by phenolate ion nucleophiles with pKas well below and above that of the leaving group is consistent with a single step mechanism.
