https://scholars.lib.ntu.edu.tw/handle/123456789/612090
Title: | Reactions of carbene-stabilized borenium cations | Authors: | Lam, Jolie Cao, Levy L. Farrell, Jeffrey M. Stephan, Douglas W. JEFFREY M. FARRELL |
Issue Date: | 2020 | Journal Volume: | 49 | Journal Issue: | 6 | Start page/Pages: | 1839-1846 | Source: | DALTON TRANSACTIONS | Abstract: | 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 borenium 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 = C4H97, 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 H2CC(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)2C6H4)2CB] 13. The implications of these findings are discussed. This journal is ? The Royal Society of Chemistry. |
URI: | https://www.scopus.com/inward/record.uri?eid=2-s2.0-85079249641&doi=10.1039%2fc9dt04731j&partnerID=40&md5=a7590144985eb9e8219750b7b694dd00 https://scholars.lib.ntu.edu.tw/handle/123456789/612090 |
DOI: | 10.1039/c9dt04731j | SDG/Keyword: | Salts; 1-hexyne; 2-vinylpyridine; Alkenyl; Carbenes; Cation salts; Cyclohexenes; Diphenylacetylene; Positive ions |
Appears in Collections: | 化學系 |
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