137266-01-4Relevant articles and documents
Halogen-lithium exchange versus deprotonation: synthesis of diboronic acids derived from aryl-benzyl ethers
Kli?, Tomasz,Serwatowski, Janusz
, p. 1169 - 1173 (2007)
Lithiation of a series of aryl benzyl ethers containing halogen substituents (-F, -Br, -I) was investigated. The resultant mono- and diorganolithium intermediates were converted into the corresponding aldehydes or diboronic acids in good yields. The dilit
Ni-Catalyzed Carbon-Carbon Bond-Forming Reductive Amination
Heinz, Christoph,Lutz, J. Patrick,Simmons, Eric M.,Miller, Michael M.,Ewing, William R.,Doyle, Abigail G.
supporting information, p. 2292 - 2300 (2018/02/19)
This report describes a three-component, Ni-catalyzed reductive coupling that enables the convergent synthesis of tertiary benzhydryl amines, which are challenging to access by traditional reductive amination methodologies. The reaction makes use of iminium ions generated in situ from the condensation of secondary N-trimethylsilyl amines with benzaldehydes, and these species undergo reaction with several distinct classes of organic electrophiles. The synthetic value of this process is demonstrated by a single-step synthesis of antimigraine drug flunarizine (Sibelium) and high yielding derivatization of paroxetine (Paxil) and metoprolol (Lopressor). Mechanistic investigations support a sequential oxidative addition mechanism rather than a pathway proceeding via α-amino radical formation. Accordingly, application of catalytic conditions to an intramolecular reductive coupling is demonstrated for the synthesis of endo- and exocyclic benzhydryl amines.
Palladium(0)-catalyzed intramolecular heck reaction: A resourceful route for the synthesis of naphthoxepine naphthoxocine derivatives
Majumdar,Ansary, Inul,Sinha, Biswajit,Chattopadhyay, Buddhadeb
experimental part, p. 3593 - 3602 (2010/03/03)
The synthesis of oxocines and oxepines is difficult. Two efficient protocols have been developed for the construction of naphthoxepine and naphthoxocine derivatives by sequential Wittig olefination and intramolecular Heck reaction. Georg Thieme Verlag Stuttgart.
