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Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
Oxidative addition of cyanogen bromide to C,N-chelated and Lappert's stannylenes
Petr Švec1, Maksim A Samsonov1, Zdeňka RůŽičková1
1Department of General and Inorganic Chemistry, Faculty of Chemical Technology, University of Pardubice, Studentská 573, CZ-532 10, Pardubice, Czech Republic. petr.svec2@upce.cz.
Abstract:
Stannylenes of L2Sn type bearing either C,N-chelating (1, L = LCN = 2-(N,N-dimethylaminomethyl)phenyl) or bulky amido (2, L = LN = N(SiMe3)2) ligands react with cyanogen bromide (Br-C[triple bond, length as m-dash]N) via an oxidative-addition reaction to give monomeric six-coordinate (LCN)2Sn(Br)CN (1a) and four-coordinate (LN)2Sn(Br)CN (2a) stannanes in moderate yields. In solution, both 1a and 2a undergo instantaneous bromido-cyanido ligand redistribution reactions, leading to mixtures containing 1a, (LCN)2SnBr2 (1b) and (LCN)2Sn(CN)2 (1c) or 2a, (LN)2SnBr2 (2b) and (LN)2Sn(CN)2 (2c), respectively. The prepared species were characterised by multinuclear NMR spectroscopy in solution (1a-c and 2a-c) and in the solid state (1a-c). The crystal structures of 1a/b/c, 2a/b/c and sole 2b were determined by XRD analyses. DFT calculations and QTAIM analysis were also carried out to corroborate the experimental results.
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