4181-90-2Relevant articles and documents
Controlling Selectivity in the Synthesis of Z-α,β-Unsaturated Amidines by Tuning the N-Sulfonyl Group in a Rhodium(II) Catalyzed 1,2-H Shift
Boyer, Alistair,Martin, Matthew L.
supporting information, p. 5857 - 5861 (2021/11/27)
N2-Sulfonyl-α-diazo amidines can be synthesized by the reaction of electron rich alkynyl amines with electron poor sulfonyl azides through 1,3-dipolar cycloaddition that proceeds with perfect regioselectivity. In the presence of rhodium(II) carboxylate catalysts, denitrogenation occurs to give the corresponding metallocarbene but there are then two competing processes: 1,2–H shift and O-transfer from the sulfonyl group to the metallocarbene center. The outcome can be controlled using an electron poor nitrobenzenesulfonyl group and large carboxylate rhodium ligands to select for 1,2–H shift, forming α,β-unsaturated amidines in high yield and with excellent Z-selectivity.
An Iron-Mesoionic Carbene Complex for Catalytic Intramolecular C-H Amination Utilizing Organic Azides
Albrecht, Martin,Keilwerth, Martin,Meyer, Karsten,Pividori, Daniel M.,Stroek, Wowa
supporting information, p. 20157 - 20165 (2021/12/09)
The synthesis of N-heterocycles is of paramount importance for the pharmaceutical industry. They are often synthesized through atom economic and environmentally unfriendly methods, generating significant waste. A less explored, but greener, alternative is
Aryl-Nickel-Catalyzed Benzylic Dehydrogenation of Electron-Deficient Heteroarenes
Zhang, Pengpeng,Huang, David,Newhouse, Timothy R.
supporting information, p. 1757 - 1762 (2020/02/04)
This manuscript describes the first practical benzylic dehydrogenation of electron-deficient heteroarenes, including pyridines, pyrazines, pyrimidines, pyridazines, and triazines. This transformation allows for the efficient benzylic oxidation of heteroarenes to afford heterocyclic styrenes by the action of nickel catalysis paired with an unconventional bromothiophene oxidant.
