1217265-45-6Relevant articles and documents
Access to Benzazepinones by Pd-Catalyzed Remote C-H Carbonylation of γ-Arylpropylamine Derivatives
Martínez-Mingo, Mario,Rodríguez, Nuria,Gómez Arrayás, Ramón,Carretero, Juan C.
, p. 4345 - 4349 (2019/06/14)
A general method for the construction of seven-membered rings through Pd-catalyzed C(sp2)-H carbonylation at the remote ?-position of γ-arylpropylamine derivatives, including chiral α-amino acids, has been developed using Mo(CO)6 as the CO source, furnishing richly functionalized benzo[c]azepin-1-one derivatives. The readily removable N-SO2Py protecting/directing group provides high levels of chemo-, regio- and diastereoselectivity. Furthermore, this method is amenable to the postsynthetic modification of complex molecules such as small peptides.
Unified mild reaction conditions for C2-selective Pd-catalysed tryptophan arylation, including tryptophan-containing peptides
Reay, Alan J.,Williams, Thomas J.,Fairlamb, Ian J. S.
, p. 8298 - 8309 (2015/08/03)
Pd-mediated C-H bond functionalisation protocols have been designed and developed on tryptophan derivatives and tryptophan-containing peptides. The examination of different arylation reactions (three sets of different conditions A-C), all of which are notable for their low temperatures (≤40°C), allowed identification of unified and complementary synthetic approaches toward a series of functionalised tryptophan-containing products. Tryptophan-containing peptides demonstrated to be susceptible to aromatic oxidation were successfully and selectively modified through the application of diaryliodonium salts in good yields.
Formation and propagation of well-defined Pd nanoparticles (PdNPs) during C-H bond functionalization of heteroarenes: Are nanoparticles a moribund form of Pd or an active catalytic species?
Baumann, Christoph G.,De Ornellas, Sara,Reeds, Jonathan P.,Storr, Thomas E.,Williams, Thomas J.,Fairlamb, Ian J.S.
, p. 6174 - 6187 (2015/04/14)
Abstract Examination of a series of C-H bond functionalization reactions of heteroarenes (e.g., indole, benzoxazole, benzthiazole, benzimidazole and purine derivatives) mediated by Pd(OAc), a commonly used C-H bond functionalization catalyst, reveals that well-defined Pd nanoparticles (PdNPs) are rapidly formed under working catalyst conditions. The PdNPs can be characterized ex situ after entrapment in a polymer matrix (polyvinylpyrrolidinone, PVP). Independently synthesized Pd(PVP)NPs are catalytically competent species, exhibiting catalyst activity commensurate with Pd(OAc) in several C-H bond functionalization reactions. Across a range of reactions, Pd concentration is a common variable, which can be linked to the propagation of PdNPs under working catalytic conditions using polar solvents like DMF, DMSO and acetic acid.