109-04-6Relevant articles and documents
Chlorierung und Bromierung von Pyridin-Palladium(II)-chlorid-Komplex
Paraskewas, Spyridon
, p. 378 - 379 (1980)
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Cl3CCN/PPh3 and CBr4/PPh3: Two efficient reagent systems for the preparation of N-heteroaromatic halides
Kijrungphaiboon, Woranun,Chantarasriwong, Oraphin,Chavasiri, Wainthorn
, p. 674 - 677 (2012)
Cl3CCN/PPh3 and CBr4/PPh3 are two highly reactive reagent systems for the conversion of N-heteroaromatic hydroxy compounds into N-heteroaromatic chlorides or bromides in moderate to excellent yields under mild and acid-free conditions.
TMSCH2Li and TMSCH2Li-LiDMAE: Efficient reagents for noncryogenic halogen-lithium exchange in bromopyridines
Doudouh, Abdelatif,Woltermann, Christopher,Gros, Philippe C.
, p. 4978 - 4980 (2007)
(Chemical Equation Presented) TMSCH2Li and TMSCH 2Li-LiDMAE have been used efficiently for bromine-lithium exchange in 2-bromo-, 3-bromo-, and 2,5-dibromopyridines under noncryogenic conditions, while low temperatures (-78 to -100°C) are always needed with n-BuLi. The aminoalkoxide LiDMAE induced a remarkable C-2 selectivity with 2,5-dibromopyridines in toluene at 0°C, which was unprecedented at such a temperature. The lithiopyridines were successfully reacted witb electrophiles also under noncryogenic conditions giving the expected adducts in good yields.
Steric Effects on the Structures, Reactivity, and Coordination Chemistry of Tris(2-pyridyl)aluminates
García-Rodríguez, Raúl,Wright, Dominic S.
, p. 14949 - 14957 (2015)
Introducing substituents in the 6-position of the 2-pyridyl rings of tris(pyridyl)aluminate anions, of the type [EtAl(2-py′)3]- (py′=a substituted 2-pyridyl group), has a large impact on their metal coordination characteristics. This is seen most remarkably in the desolvation of the THF solvate [EtAl(6-Me-2-py)3Li·THF] to give the monomer [EtAl(6-Me-2-py)3Li] (1), containing a pyramidal, three-coordinate Li+ cation. Similar monomeric complexes are observed for [EtAl(6-CF3-2-py)3Li] (2) and [EtAl(6-Br-2-py)3Li] (3), which contain CF3 and Br substituents (R). This steric influence can be exploited in the synthesis of a new class of terminal Al-OH complexes, as is seen in the controlled hydrolysis of 2 and 3 to give [EtAl(OH)(6-R-2-py)2]- anions, as in the dimer [EtAl(OH)(6-Br-2-py)2Li]2 (5). Attempts to deprotonate the Al-OH group of 5 using Et2Zn led only to the formation of the zincate complex [LiZn(6-Br-py)3]2 (6), while reactions of the 6-Br substituted 3 and the unsubstituted complex [EtAl(2-py)3Li] with MeOH give [EtAl(OMe)(6-Br-2-py)2Li]2 (7) and [EtAl(OMe)(2-py)2Li]2 (8), respectively, having similar dimeric arrangements to 5. The combined studies presented provide key synthetic methods for the functionalization and elaboration of tris(pyridyl)aluminate ligands.
A facile bromination of hydroxyheteroarenes
Kato, Yoshiaki,Okada, Shigemitsu,Tomimoto, Koji,Mase, Toshiaki
, p. 4849 - 4851 (2001)
Bromination of hydroxyheteroarenes using P2O5/Bu4NBr proceeds under mild conditions to afford high yields of various bromoheteroarenes. This procedure is successfully applied to large-scale syntheses of bromoheteroarenes.
Transition-metal-free decarboxylative halogenation of 2-picolinic acids with dihalomethane under oxygen conditions
Zhang, Xitao,Feng, Xiujuan,Zhang, Haixia,Yamamoto, Yoshinori,Bao, Ming
supporting information, p. 5565 - 5570 (2019/10/22)
A convenient and efficient method for the synthesis of 2-halogen-substituted pyridines is described. The decarboxylative halogenation of 2-picolinic acids with dihalomethane proceeded smoothly via N-chlorocarbene intermediates to afford 2-halogen-substituted pyridines in satisfactory to excellent yields under transition-metal-free conditions. This new type of decarboxylative halogenation is operationally simple and exhibits high functional-group tolerance.
Synthesis of bromocyclopropylpyridines via the Sandmeyer reaction
Striela, Romualdas,Urbelis, Gintaras,Sūd?ius, Jurgis,Ston?ius, Sigitas,Sadzevi?ien?, Rita,Labanauskas, Linas
supporting information, p. 1681 - 1683 (2017/04/06)
The reactions of 2-amino-5-cyclopropylpyridine with organic nitrites in the presence of copper(II) halides in various organic solvents were investigated. Optimal reaction conditions for the Sandmeyer reaction were developed and successfully applied to the synthesis of useful building blocks, bromo and chlorocyclopropylpyridines. Aminocyclopropylpyridines were synthesized in high yields from the corresponding aminobromopyridines under standard Suzuki coupling conditions.