33421-20-4Relevant academic research and scientific papers
A solution to the 2-pyridyl organometallic cross-coupling problem: Regioselective catalytic direct arylation of pyridine N-oxides
Campeau, Louis-Charles,Rousseaux, Sophie,Fagnou, Keith
, p. 18020 - 18021 (2005)
Direct arylation reactions of pyridine N-oxides occur in excellent yield with complete selectivity for the 2-position with a wide range of aryl bromides. This reactivity permits the use of inexpensive, commercially available, and bench-stable pyridine N-oxides as replacements for problematic 2-metallapyridines in palladium-catalyzed cross-coupling reactions. Copyright
2,2′-Homocoupled Azine N,N′-Dioxides or Azine N-Oxides: CDC- or SNAr-Controlled Chemoselectivity
Jha, Abadh Kishor,Jain, Nidhi
, p. 4765 - 4772 (2017/09/07)
An unprecedented Cu(OAc)2- and LiOtBu-mediated homocoupling of azine N-oxides to yield 2,2′-azine N,N′-dioxides is reported. This is the first instance in which copper has been used to catalyze the homodimerization reaction, especially of 2-phenylpyridine N-oxides. In the absence of catalytic copper, the reaction follows an alternative pathway, and instead of dioxides it yields 2,2′-azine N-monoxides. This latter protocol works efficiently with a range of N-heterocyclic oxides of pyridine, 2-phenylpyridine, quinoline and N-aryl-1,2,3-triazole. It is scalable, offers high regioselectivity and gives the products in moderate to high yields. The observed chemoselectivity between the copper-assisted and copper-free protocols is routed through oxidative cross-dehydrogenative coupling (CDC) and nucleophilic aromatic substitution of hydrogen (SNAr) pathways, respectively.
Silver-catalyzed 2-pyridyl arylation of pyridine N-oxides with arylboronic acids at room temperature
Mai, Wenpeng,Yuan, Jinwei,Li, Zhicheng,Sun, Gangchun,Qu, Lingbo
supporting information; experimental part, p. 145 - 149 (2012/02/04)
A novel direct arylation of pyridine N-oxides with arylboronic acids through C-H functionalization has been developed. This new reaction is performed at room temperature using catalytic silver(I) nitrate in the presence of potassium persulfate and give 2-
Substitution of the nitro group with Grignard reagents: Facile arylation and alkenylation of pyridine N-oxides
Zhang, Fang,Zhang, Song,Duan, Xin-Fang
, p. 5618 - 5620 (2013/01/15)
The unprecedented substitution of a nitro group with aryl or alkenyl groups of Grignard reagents affords 2-aryl or alkenylpyridine N-oxides in modest to high yields with high chemoselectivity. This protocol allows a simple and clean synthesis of various 2
Use of N-oxide compounds in coupling reactions
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Page/Page column 7-8, (2008/12/05)
Metal-catalyzed coupling process comprising reacting a compound of general formula 1 with a compound A-X, to obtain a compound of general formula 2, which may further be converted to a compound of general formula 3
