54015-96-2Relevant articles and documents
Efficient and regioselective access to bis-heterocycles via palladium- catalysed coupling of organostannanes and organozincates derived from C-6 lithiated 2-methoxypyridine
Gros, Philippe,Fort, Yves
, p. 754 - 756 (1999)
The efficient and regioselective synthesis of various bis-heterocyclic compounds was performed using a regioselective one-pot lithiation- transmetallation-cross-coupling of 2-methoxypyridine.
Stabilization and destabilization of the Ru-CO bond during the 2,2′-bipyridin-6-onato (bpyO)-localized redox reaction of [Ru(terpy)(bpyO)(CO)](PF6)
Tomon, Takashi,Koizumi, Take-Aki,Tanaka, Koji
, p. 285 - 293 (2005)
Two stereoisomers of [Ru(terpy)(bpyO)(CO)](PF6)([1]+ and [2]+; terpy = 2,2′:6′,2″-terpyridine, bpyO = 2,2′-bipyridin-6-onato) were prepared. The pyridonato moiety in the bpyO ligand of [1]+ and [2]+ is located trans and cis, respectively, to CO. Treatment of [1]+ and [2]+ with HPF6 produced [1H]2+ and [2H]2+, both of which contain bpyOH (bpyOH = 6-hydroxy-2,2′-bipyridine). The difference in the pKa values of [1H]2+ (3.5) and [2H]2+ (3.9) reflects the stronger electronic interaction between CO and the pyridonato moiety in the bpyO ligand in the trans position compared with that in the cis position. The molecular structures of [1](PF6), [2](PF 6)·H2O and [2H](PF6)2· 2H2O were determined by X-ray structure analyses. [1]+ and [2]+ undergo one, reversible reduction at E1/2 = -1.65 V and -1.51 V, respectively, and one irreversible reduction at Ep,c = -2.07 and Ep,c = -2.13 V, respectively. Both reductions are assigned to redox reactions localized at the terpy and bpyO ligands. Irreversible reduction of [1]0 results from reductive cleavage of the Ru-CO bond of [1]-. On the other hand, a two-electron oxidation of [2] - almost regenerates [2]+ because of the depression of the reductive Ru-CO bond cleavage of [2]- due to cyclometalation formed by an attack of oxygen of bpyO to the carbon of the Ru-CO bond. An unusually large shift of the ν(C≡O) band on going from [2]0 (1950 cm-1) to [2]- (1587 cm-1) also supports a reversible cyclometalation driven by the bpyO-localized redox reaction. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.
Rhodium(iii)-catalyzed switchable C-H acylmethylation and annulation of 2,2′-bipyridine derivatives with sulfoxonium ylides
Chen, Chen,Chen, Mengjia,Meng, Haifang,Wang, Yani,Yang, Fang,Zhu, Bolin
supporting information, p. 4268 - 4271 (2021/05/31)
A novel protocol for Rh(iii)-catalyzed switchable C-H acylmethylation and annulation of 2,2′-bipyridine derivatives with sulfoxonium ylides is reported. This protocol provides a facile approach to synthesize structurally diverse acylmethylated 2,2′-bipyridine derivatives and acyl pyrido[2,3-a]indolizines with a broad range of functional group tolerance.
A novel approach for rhodium(iii)-catalyzed C-H functionalization of 2,2′-bipyridine derivatives with alkynes: A significant substituent effect
Wu, Shaonan,Wang, Zhuo,Bao, Yinwei,Chen, Chen,Liu, Kun,Zhu, Bolin
supporting information, p. 4408 - 4411 (2020/05/05)
We described a novel approach for the C-H functionalization of 2,2′-bipyridine derivatives with alkynes. DFT calculations and experimental data showed a significant substituent effect at the 6-position of 2,2′-bipyridine, which weakened the adjacent N-Rh bond and provided the possibility of subsequent rollover cyclometalation, C-H activation, and functionalization.
