113964-72-0Relevant articles and documents
Phosphonium Salts as Pseudohalides: Regioselective Nickel-Catalyzed Cross-Coupling of Complex Pyridines and Diazines
Zhang, Xuan,McNally, Andrew
supporting information, p. 9833 - 9836 (2017/08/08)
Heterobiaryls are important pharmacophores that are challenging to prepare by traditional cross-coupling methods. An alternative approach is presented where pyridines and diazines are converted into heteroaryl phosphonium salts and coupled with aryl boronic acids. Nickel catalysts are unique for selective heteroaryl transfer, and the reaction has a broad substrate scope that includes complex pharmaceuticals. Phosphonium ions also display orthogonal reactivity in cross-couplings compared to halides, enabling chemoselective palladium- and nickel-catalyzed coupling sequences.
Chemistry of Triphenyl-(or Tri-n-butyl)pyridylphosphonium Salts, 1. - Novel Method for the Regioselective Introduction of Phosphonium Groups into N-Heteroaromatic Ring Systems
Anders, Ernst,Markus, Fritz
, p. 113 - 118 (2007/10/02)
N-Triflyl-heteroarylium triflates such as 3b and analogous salts of pyrazine, benzothiazole, and quinoline are transformed by regioselective reactions with phosphanes 4a and b into the title compounds 15a-f or 16, 17, 18a and b, respectively.With the salt 26 this reaction can be repeated to give the bis-cationic species 28a or b.Using the salt 15a as a representative, some aspects of the chemistry of heteroaryltriphenylphosphonium salts are described: Starting with the common precursor 15a, 2-acylated pyridines 21, 4,4'-bipyridines 23, and pyridylcarbinols 25 are accessible besides 28. - Keywords: Phosphonium groups, introduction into N-heteroaromatic rings / Pyridylphosphonium salts, tri-n-butyl- and triphenyl-
NEUE METHODE ZUR REGIOSPEZIFISCHEN SUBSTITUTION EINIGER REAKTIONSTRAEGER N-HETEROAROMATISCHER RINGSYSTEME
Anders, Ernst,Markus, Fritz
, p. 2675 - 2676 (2007/10/02)
N-Trifluoromethanesulfonyl-heteroarylium salts 1 react with phosphanes 2 to give the C4- or C2-substituted products 4 or 5.By means of a similar procedure, bisphosphonium salts 6 and 7 are formed.The reaction of sodium azide (8), and 6 yields the iminophosphorane 10 via the intermediate 9.