51581-40-9Relevant academic research and scientific papers
N -Arylation of (hetero)arylamines using aryl sulfamates and carbamates via C-O bond activation enabled by a reusable and durable nickel(0) catalyst
Dindarloo Inaloo, Iman,Majnooni, Sahar,Eslahi, Hassan,Esmaeilpour, Mohsen
, p. 13266 - 13278 (2020/10/07)
An effective and general aryl amination protocol has been developed using a magnetically recoverable Ni(0) based nanocatalyst. This new stable catalyst was prepared on Fe3O4@SiO2 modified by EDTA and investigated by FT-IR, EDX, TEM, XRD, DLS, FE-SEM, XPS, NMR, TGA, VSM, ICP and elemental analysis techniques. The reaction proceeded via carbon-oxygen bond cleavage of (hetero)aryl carbamates and sulfamates under simple and mild conditions without the use of any external ligands. This method demonstrated functional group tolerance in the N-arylation of various nitrogen-containing compounds as well as aliphatic amines, anilines, pyrroles, pyrazoles, imidazoles, indoles, and indazoles with good to excellent yields. Furthermore, the catalyst could be easily recovered by using an external magnetic field and directly reused at least six times without notable reduction in its activity. This journal is
Nickel-catalyzed cross-coupling reaction of carbamates with silylmagnesium reagents
Murugesan, Vetrivelan,Balakrishnan, Venkadesh,Rasappan, Ramesh
, p. 293 - 298 (2019/08/12)
The C–O bonds are kinetically inert in cross-coupling reactions compared to those of carbon–halogen bonds. Thus, developing methodologies for the activation of C–O bonds in cross-coupling reactions remains a major challenge. We disclose an unprecedented nickel mediated cross-coupling of carbamates with silylmagnesium reagents that does not require the expensive silylboranes. Silylmagnesium reagents were prepared from either silyllithium or silyl iodides. This methodology is distinguished by the synthesis of trimethylsilyl coupled product and its synthetic applications. Kinetic studies and radical clock experiments revealed the rate-limiting C–O bond cleavage, half order with respect to the catalyst and a non-radical transition state.
Combined directed ortho metalation-halogen dance (HD) synthetic strategies. HD-anionic ortho fries rearrangement and double HD sequences
Miller, Ricarda E.,Rantanen, Toni,Ogilvie, Kevin A.,Groth, Ulrich,Snieckus, Victor
supporting information; experimental part, p. 2198 - 2201 (2010/08/06)
A general and efficient directed ortho metalation (DoM)-halogen dance (HD)-electrophile quench sequence for the synthesis of trisubstituted pyridyl O-carbamates is described. A second HD sequence furnishes highly functionalized tetrasubstituted pyridines.
Synthesis and nicotinic acetylcholine receptor binding properties of bridged and fused ring analogues of epibatidine
Carroll, F. Ivy,Robinson, T. Philip,Brieaddy, Lawrence E.,Atkinson, Robert N.,Mascarella, S. Wayne,Damaj, M. Imad,Martin, Billy R.,Navarro, Hernán A.
, p. 6383 - 6391 (2008/03/30)
Epibatidine analogues 3-5, possessing the pyridine ring fused to the 2,3 position of the 7-azabicyclo[2.2.1]heptane ring, and analogue 8a, possessing a benzene ring fused to the 5,6 position, were synthesized by procedures involving key steps of trapping
Synthesis of two conformationally constrained analogues of the minor tobacco alkaloid anabasine.
Lindstroem,Ripa,Hallberg
, p. 2291 - 2293 (2007/10/03)
The anabasine analogues spiro[4-azaindan-1,2'-piperidine] (7) and spiro[6-azaindan-1,2'-piperidine] (8) have been prepared. A series of palladium-catalyzed reactions, where an intramolecular cyclization constituted a key reaction, were utilized for the pr
3-pyridyloxymethyl heterocyclic ether compounds useful in controlling neurotransmitter release
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, (2008/06/13)
Novel heterocyclic ether compounds of the formula: STR1 wherein n, *, R1, R2, R3 and y are specifically defined, or pharmaceutically acceptable salts or prodrugs thereof, which are useful in selectively controlling neurotransmitter release; therapeutically-effective pharmaceutical compositions of these compounds; and use of said compositions to selectively control neurotransmitter release in mammals.
