21172-82-7Relevant academic research and scientific papers
Pd-Catalyzed Decarboxylation and Dual C(sp3)-H Functionalization Protocols for the Synthesis of 2,4-Diarylpyridines
Gujjarappa, Raghuram,Vodnala, Nagaraju,Kumar, Mohan,Malakar, Chandi C.
, p. 5005 - 5020 (2019/04/25)
The Pd-catalyzed decarboxylation and dual C(sp3)-H bond functionalization approaches have been described for the preparation of symmetrical and unsymmetrical 2,4-diarylpyridines. The developed transformations were realized using nonactivated aromatic ketones and amino acids as C-N sources. The efficacy of the catalyst and reagent combination drives the transformation toward the formation of desired products with high yields and selectivity. The described reaction conditions have seduced the self-reaction of phenylalanine via [2 + 2 + 2] cycloaddition and minimized the formation of 3,5-phenylpyridine as a side product, whereas using glycine as a C-N source, the corresponding 2,6-diarylpyridines were formed as minor products.
Cross-coupling study of iodo/chloropyridines and 2-chloroquinoline with atom-economic triarylbismuth reagents under Pd-catalysis
Rao, Maddali L.N.,Dhanorkar, Ritesh J.
, p. 338 - 349 (2015/03/04)
This study describes the palladium-catalyzed couplings of iodopyridines, chloropyridines, and chloroquinoline with atom-economic BiAr3 reagents in sub-stoichiometric loadings. Mono-arylations of iodo and chloropyridines produced arylpyridines i
Triarylbismuthanes as threefold aryl-transfer reagents in regioselective cross-coupling reactions with bromopyridines and quinolines
Rao, Maddali L.N.,Dhanorkar, Ritesh J.
, p. 5214 - 5228 (2014/10/15)
Cross-coupling studies using bromopyridines and bromoquinolines with triarylbismuths as threefold coupling reagents in substoichiometric amounts under Pd-catalysed conditions are disclosed. The reactivity was high with both mono- and dibromopyridyl substrates, and mono- and bis-couplings were carried out regioselectively. A library of monoaryl and diaryl pyridines was formed in high yields. A one-pot strategy provided a simple and straightforward synthesis of both symmetrical and unsymmetrical diarylpyridines. Arylations of 2-bromo- and 3-bromoquinolines were achieved with triarylbismuth reagents. This study demonstrates that triarylbismuths may be used as threefold arylating reagents for the synthesis of aryl pyridines and quinolines through couplings with bromopyridines and bromoquinolines under Pd-catalysed conditions. Copyright
Selective Suzuki-Miyaura monocouplings with symmetrical dibromoarenes and aryl ditriflates for the one-pot synthesis of unsymmetrical triaryls
Minard, Corinne,Palacio, Carole,Cariou, Kevin,Dodd, Robert H.
, p. 2942 - 2955 (2014/05/20)
The various parameters that would permit selective Suzuki-Miyaura monocouplings of symmetrical dihaloarenes were studied. High selectivity and efficiency can be obtained for a broad range of substrates by using operationally simple conditions and widely available reagents. The 38 different examples described provide a valuable toolbox for the rapid access to unsymmetrical triaryls, as illustrated by the preparation of diarylpyridine 8, terphenyl 9, and diarylpyrrole 10. By studying several key parameters, the factors that allow selective Suzuki-Miyaura monocoupling of symmetrical dihaloarenes have been outlined. This study serves as the basis for the efficient synthesis of unsymmetrical triaryls from symmetrical dibromoarenes and aryl ditriflates by a one-pot desymmetrizing double Suzuki-Miyaura coupling. Copyright
