36995-45-6Relevant academic research and scientific papers
Acylation of 2-benzylpyridine N-oxides and subsequent in situ [3,3]-sigamatropic rearrangement reaction
Antilla, Jon C.,Jing, Hua-qing,Li, Hong-liang
, (2020/09/22)
An effective method for the acylation of 2-benzylpyridine N-oxides and their fast in situ [3,3]-sigmatropic rearrangement was reported. This transformation has a wide substrate scope under mild conditions, giving moderate to excellent yields. The application for the synthesis of chiral phenyl-2-pyridylmethanol products was briefly explored. Furthermore, an interesting example of tandem substitution and in situ [3,3]-sigamatropic rearrangement of 2-benzylpyridine N-oxide with benzenecarboximidoyl chloride was reported.
Ligand-Free Iridium-Catalyzed Dehydrogenative ortho C?H Borylation of Benzyl-2-Pyridines at Room Temperature
Yang, Yuhuan,Gao, Qian,Xu, Senmiao
, p. 858 - 862 (2019/01/04)
A convenient and ligand-free iridium-catalyzed dehydrogenative ortho C?H borylation of benzyl-2-pyridines has been developed. The reaction proceeds smoothly at room temperature using pinacolborane as a borylating reagent in the presence of catalytic amount of [IrOMe(COD)]2. The reaction is compatible with many functional groups, providing a vast array of ortho borylated products in moderate to excellent yields with excellent selectivities. (Figure presented.).
Palladium-Catalyzed Arylation of Benzylic C-H Bonds of Azaarylmethanes with Aryl Sulfides
Gao, Ke,Yamamoto, Keita,Nogi, Keisuke,Yorimitsu, Hideki
supporting information, p. 2956 - 2960 (2017/10/06)
Benzylic C-H arylation of azaarylmethanes with aryl sulfides has been developed by using a Pd-NHC catalyst and an amide base. Various azaarylmethanes and aryl sulfides were involved in the reaction to afford the corresponding diarylmethanes in good to excellent yields. Moreover, triarylmethane synthesis was accomplished through iterative arylations of 2- or 4-methylpyridine with two different aryl sulfides.
Direct Triflylation of Benzylic C—H Bonds with Pyridine as a Directing Group
Yang, Jun,Hu, Juanjuan,Huang, Yangen,Xu, Xiuhua,Qing, Fengling
supporting information, p. 867 - 870 (2017/06/27)
The first example of benzylic C—H triflylation was accomplished with pyridine as a directing group. The reaction of various 2-benzylpyridines and (CF3SO2)2O in the presence of NEt3 in CH2Cl2 proceeded smoothly to afford the corresponding benzyl triflones in moderate to high yields.
Versatile C(sp2)?C(sp3) Ligand Couplings of Sulfoxides for the Enantioselective Synthesis of Diarylalkanes
Dean, William M.,?iau?iulis, Mindaugas,Storr, Thomas E.,Lewis, William,Stockman, Robert A.
supporting information, p. 10013 - 10016 (2016/08/16)
The reaction of chiral (hetero)aryl benzyl sulfoxides with Grignard reagents affords enantiomerically pure diarylalkanes in up to 98 % yield and greater than 99.5 % enantiomeric excess. This ligand coupling reaction is tolerant to multiple substitution patterns and provides access to diverse areas of chemical space in three operationally simple steps from commercially available reagents. This strategy provides orthogonal access to electron-deficient heteroaromatic compounds, which are traditionally synthesized by transition metal catalyzed cross-couplings, and circumvents common issues associated with proto-demetalation and β-hydride elimination.
Synthesis of heteroaryl compounds through cross-coupling reaction of aryl bromides or benzyl halides with thienyl and pyridyl aluminum reagents
Chen, Xu,Zhou, Lingmin,Li, Yimei,Xie, Tao,Zhou, Shuangliu
, p. 230 - 239 (2014/01/17)
An efficient method for synthesis of useful biaryl building blocks containing 2-thienyl, 3-thienyl, 2-pyridyl, and 3-pyridyl moieties was provided through cross-coupling reactions of aryl bromides or benzyl halides with heteroaryl aluminum reagents in the presence of Pd(OAc)2 and (o-tolyl)3P. The coupling reaction also worked efficiently with heteroaryl bromides affording series of heterobiaryl compounds. The reaction of phenylbromide with in situ prepared 3-pyridyl aluminum was demonstrated to afford the product 8a in high yield. Additionally, the catalytic system was also suited well for the coupling reaction of benzyl halides with pyridyl aluminum reagents to afford series of pyridyl-arylmethane.
Palladium-catalyzed 2-pyridylmethyl transfer from 2-(2-pyridyl)-ethanol derivatives to organic halides by chelation-assisted cleavage of unstrained Csp3-Csp3 bonds
Niwa, Takashi,Yorimitsu, Hideki,Oshima, Koichiro
, p. 2643 - 2645 (2008/02/13)
(Chemical Equation Presented) Making a break for it: Treatment of 2-(2-pyridyl)ethanol derivatives with aryl chlorides in the presence of a palladium catalyst results in the transfer of the pyridylmethyl moiety of the alcohol to yield the corresponding (2-pyridyl-methyl)arene. The reaction proceeds by chelation-assisted cleavage of an Csp3-C5p3 bond (see scheme) followed by formation of a carbon-carbon bond.
Flash Vacuum Pyrolysis of Substituted Pyridine N-Oxides and Its Application to Syntheses of Heterocyclic Compounds
Ohsawa, Akio,Kawaguchi, Takayuki,Igeta, Hiroshi
, p. 3497 - 3503 (2007/10/02)
Flash vacuum pyrolysis of 2-picoline N-oxide gave 2-picoline, pyridine, 2-ethylpyridine, 2-vinylpyridine, 2-pyridylmethanol, bis(2-pyridyl)methane, 1,2-bis(2-pyridyl)ethane, and 1,2-bis(2-pyridyl)ethylene.These reactions are explained by intermediary participation of the 2-picolyl radical.Flash vacuum pyrolysis of methyl-substituted 2-benzylpyridine N-oxides led to methyl-substituted pyridoindoles or to benzoquinoline in moderate yields.
