Hoveyda–Grubbs catalysts with an N→Ru coordinate bond in a six-membered ring. Synthesis of stable, industrially scalable, highly efficient ruthenium metathesis catalysts and 2-vinylbenzylamine ligands as their precursors
A novel and efficient approach to the synthesis of 2-vinylbenzylamines is reported. This involves obtaining 2-vinylbenzylamine ligands from tetrahydroisoquinoline by alkylation and reduction followed by the Hofmann cleavage. The resultant 2-vinylbenzyl-amines allowed us to obtain new Hoveyda–Grubbs catalysts, which were thoroughly characterised by NMR, ESIMS, and X-ray crystallography. The utility of this chemistry is further demonstrated by the tests of the novel catalysts (up to 10?2 mol %) in different metathesis reactions such as cross metathesis (CM), ring-closing metathesis (RCM) and ring-opening cross metathesis (ROCM).
Polyanskii, Kirill B.,Alekseeva, Kseniia A.,Raspertov, Pavel V.,Kumandin, Pavel A.,Nikitina, Eugeniya V.,Gurbanov, Atash V.,Zubkov, Fedor I.
supporting information
p. 769 - 779
(2019/04/17)
A one-pot domino reaction for the synthesis of 3-arylindolizines from pyridines, benzyl halides, and dihalide-substituted electron-deficient alkenes
3-Arylindolizines were prepared by one-pot domino reactions from benzyl halides with pyridine (or isoquinoline) and cyclic or acyclic dihalide-substituted electron-deficient alkenes in the presence of potassium carbonate via in situ generated N-ylide intermediate. Both electron-donating and electron-withdrawing groups are tolerated in the aryl ring of benzyl halides. The yields range from moderate to high. Georg Thieme Verlag Stuttgart - New York.