3 years ago

Phosphine–Borane Frustrated Lewis Pairs Derived from a 1,1′-Disubstituted Ferrocene Scaffold: Synthesis and Hydrogenation Catalysis

Phosphine–Borane Frustrated Lewis Pairs Derived from a 1,1′-Disubstituted Ferrocene Scaffold: Synthesis and Hydrogenation Catalysis
Petr Štěpnička, Ivana Císařová, Zhongbao Jian, Gerald Kehr, Karel Škoch, Sergei Krupski, Gerhard Erker, Constantin G. Daniliuc
(Dimesitylphosphino)ferrocene (FcPMes2) (1) reacted with HB(C6F5)2 (2 equiv) by disproportionation to give adduct FcPMes2·H2B(C6F5) (4) plus B(C6F5)3, whereas 1-(dimesitylphosphino)-1′-vinylferrocene (2) was cleanly hydroborated with HB(C6F5)2 to afford [Fe(η5-C5H4PMes2)(η5-C5H4CH2CH2B(C6F5)2)] (7). Compound 7 adopted an open non-interacting P/B frustrated Lewis pair (FLP) structure in the crystal state as well as in a solution. This frustrated Lewis pair heterolytically cleaved dihydrogen under mild conditions to give the respective zwitterionic [P]H+/[B]H phosphonium/hydroborate product, [Fe(η5-C5H4PHMes2){η5-C5H4CH2CH2BH(C6F5)2}] (8), which served as a catalyst for the hydrogenation of the electron-rich π-systems (imine, enamine) as well as the electron-deficient carbon–carbon double and triple bonds in some enones and an ynone under more forcing conditions (50 bar H2 pressure, 50 °C).

Publisher URL: http://dx.doi.org/10.1021/acs.organomet.7b00363

DOI: 10.1021/acs.organomet.7b00363

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