22282-62-8Relevant academic research and scientific papers
Direct Transformation of Arylamines to Aryl Halides via Sodium Nitrite and N-Halosuccinimide
Mukhopadhyay, Sushobhan,Batra, Sanjay
supporting information, p. 14622 - 14626 (2018/09/21)
A one-pot universal approach for transforming arylamines to aryl halides via reaction with sodium nitrite (NaNO2) and N-halosuccinimide (NXS) in DMF at room temperature under metal- and acid-free condition is described. This new protocol that is complementary to the Sandmeyer reaction, is suggested to involve the in situ generation of nitryl halide induce nitrosylation of aryl amine to form the diazo intermediate which is halogenated to furnish the aryl halide.
Cheap and easy synthesis of highly functionalized (het)aryl iodides via the aromatic finkelstein reaction
Meyer-Eppler, Georg,Kuechler, Lea,Tenten, Christina,Benkhaeuser, Christian,Brueck, Stefanie,Luetzen, Arne
, p. 1085 - 1090 (2014/05/06)
Aryl iodides are superior coupling partners in cross-couplingA- reactions compared to the corresponding chlorides or bromides. Unfortunately, the iodides are much more expensive, if commercially available at all, than the other halides. Thus, it is often mandatory to transform the available bromides into the corresponding iodides. The copper-catalyzed aromatic Finkelstein reaction turned out to be the method of choice to prepare a number of highly functionalized iodo(het)aryls, including pyridines, 2,2′-bipyridines, and chiral compounds. Georg Thieme Verlag Stuttgart? New York.
Complex-induced proximity effect in the regioselective lithiation of pyridine derivatives
Dhau, Jaspreet S.,Singh, Amritpal,Kasetti, Yoganjaneyulu,Bharatam
, p. 1746 - 1752 (2012/05/04)
The regioselective ring lithiation of BF3-complexed 3-picoline (1a), 3,4-lutidine (1b), and 3,5-lutidine (1c) was studied. The dilithiation of 1a, 1b, and 1c was also investigated to experimentally explore the relative preference of the sites on the substituted pyridine ring for lithiation. The role of the complex-induced proximity effect (CIPE) for inducing lithiation in these moieties was investigated using both experimental and computational studies.
Unprecedented C-6 functionalisation of 3-picoline induced by a methyl to C-6 lithium shift
Mathieu, Julien,Gros, Philippe,Fort, Yves
, p. 951 - 952 (2007/10/03)
BuLi-Me2N(CH2)2OLi (BuLi-LiDMAE) promoted the clean C-6 functionalisation of 3-picoline via a methyl to C-6 lithium shift.
