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Reactions of Carbene-Stabilized Borenium Cations


In this paper we probe the reactivity of the borenium cations [C3H2(NCH2C6H4)(NCH2Ph)BH][B(C6F5)4] 2 and [C3H2(NCH2C6H4)2B][B(C6F5)4] 3. The reactions of 2 with cyclohexene or 3,3-dimethyl-1-butene gave the alkyl-aryl borneium salts [PhCH2(CHN)2CCH2C6H4BR][B(C6F5)4] (R = Cy 4, CH2CH2tBu 5) while the corresponding reactions with diphenylacetylene, 1-hexyne and 1-phenyl-1-propyne gave the aryl-alkenyl borenium cation salts [PhCH2(CHN)2CCH2C6H4BC(R1)C(H)R2][B(C6F5)4] (R1 = R2 = Ph 6, R1 = H, R2 = C4H9 7, R1 = Me, R2 = Ph 8a, R1 = Ph, R2 = Me 8b). In contrast, the reaction of 2 with ethynyldiphenylphosphane or 2-vinylpyridine lead to the formation of the adducts, [PhCH2(CHN)2CCH2C6H4B(H)P(Ph2)CCH][B(C6F5)4] 9, [PhCH2(CHN)2CCH2C6H4B(H)NC5H4C(H)CH2][B(C6F5)4] 10, respectively, while the more bulky donor H2C=C(Ph)PMes2 gave 1,2-hydroboration of the phosphinoalkene affording [PhCH2(CHN)2CCH2C6H4BCH2CH(Ph)PMes2][B(C6F5)4] 11. In another vein of reactivity, one or two equivalents of the FLP, PtBu3/B(C6F5)3 is shown to react with 3 to give the zwitterionic borenium-borate species [C2H2(NCH(BC(CHNCH2C6H4)2)C6H4)(NCH(B(C6F5)3)C6H4)CB] 12 and the anionic bis-borate species[tBu3PH][C2H2(NCH(B(C6F5)3)2CB] 13. The implications of these findings are discussed.

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Article information

12 Dec 2019
13 Jan 2020
First published
14 Jan 2020

Dalton Trans., 2020, Accepted Manuscript
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Reactions of Carbene-Stabilized Borenium Cations

J. Lam, L. Cao, J. Farrell and D. W. Stephan, Dalton Trans., 2020, Accepted Manuscript , DOI: 10.1039/C9DT04731J

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