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Probing the Limits of Oxidative Addition of C(sp3)–X Bonds toward Selected N,C,N-Chelated Bismuth(I) Compounds

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posted on 2020-08-04, 15:44 authored by Martin Hejda, Robert Jirásko, Aleš Růžička, Roman Jambor, Libor Dostál
The reactivity of two N,C,N-chelated bismuthinidenes, that is, [2,6-(tBuNCH)2C6H3]Bi (1) and its metastable analogue [2,6-(Me2NCH2)2C6H3]­Bi (2), toward organic substrates containing C­(sp3)–X bond (where X = I or OTf) is reported. The aim of this study is to prove the potential of the Bi­(I) center in 1 and 2 to participate in an oxidative addition toward C–X bonds under formation of corresponding trivalent bismuth compounds. The influence of the substrate is examined; thus, simple primary alkyls (including fluorinated ones) as well as more branched substrates are considered to find the limits of these reactions and recognize the differences in the reactivity between 1 and 2. All products were characterized by means of high-resolution electrospray ionization mass spectrometry (ESI-MS); 1H, 13C, and 19F NMR spectroscopy; and single-crystal X-ray diffraction analysis.

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