1599475-62-3Relevant academic research and scientific papers
Formylborane formation with frustrated Lewis pair templates
Sajid, Muhammad,Kehr, Gerald,Daniliuc, Constantin G.,Erker, Gerhard
, p. 1118 - 1121 (2014)
Boranes R2BH react with carbon monoxide by forming the respective borane carbonyl compounds R2BH(CO). The formation of (C6F5)2BH(CO) derived from the Piers borane, HB(C6F5)2, is a typical example. Subsequent CO-hydroboration does not take place, since the formation of the formylborane is usually endothermic. However, an η2-formylborane was formed by CO-hydroboration with the Piers borane at vicinal phosphane/borane frustrated Lewis pair (FLP) templates. Subsequent treatment with pyridine liberated the intact formylborane from the FLP framework, and (pyridine)(C 6F5)2B-CHO was then isolated as a stable compound. This product underwent typical reactions of carbonyl compounds, such as Wittig olefination. Channeling frustration into productivity: An elusive borane carbaldehyde was liberated from the product of carbon monoxide hydroboration at a frustrated Lewis pair template by treatment with pyridine and isolated as the donor-stabilized adduct (see scheme; Mes=mesityl). In this way, the thermodynamic restrictions of CO insertion into boron-hydrogen bonds could be circumvented. Copyright
