Formylborane Formation with Frustrated Lewis Pair Templates†
Dr. Muhammad Sajid
Organisch-Chemisches Institut der Universität Münster, Corrensstrasse 40, 48149 Münster (Germany)
Search for more papers by this authorDr. Gerald Kehr
Organisch-Chemisches Institut der Universität Münster, Corrensstrasse 40, 48149 Münster (Germany)
Search for more papers by this authorDr. Constantin G. Daniliuc
Organisch-Chemisches Institut der Universität Münster, Corrensstrasse 40, 48149 Münster (Germany)
X-ray crystal-structure analysis.
Search for more papers by this authorCorresponding Author
Prof. Dr. Gerhard Erker
Organisch-Chemisches Institut der Universität Münster, Corrensstrasse 40, 48149 Münster (Germany)
Organisch-Chemisches Institut der Universität Münster, Corrensstrasse 40, 48149 Münster (Germany)Search for more papers by this authorDr. Muhammad Sajid
Organisch-Chemisches Institut der Universität Münster, Corrensstrasse 40, 48149 Münster (Germany)
Search for more papers by this authorDr. Gerald Kehr
Organisch-Chemisches Institut der Universität Münster, Corrensstrasse 40, 48149 Münster (Germany)
Search for more papers by this authorDr. Constantin G. Daniliuc
Organisch-Chemisches Institut der Universität Münster, Corrensstrasse 40, 48149 Münster (Germany)
X-ray crystal-structure analysis.
Search for more papers by this authorCorresponding Author
Prof. Dr. Gerhard Erker
Organisch-Chemisches Institut der Universität Münster, Corrensstrasse 40, 48149 Münster (Germany)
Organisch-Chemisches Institut der Universität Münster, Corrensstrasse 40, 48149 Münster (Germany)Search for more papers by this authorFinancial support from the European Research Council is gratefully acknowledged.
Graphical Abstract
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.
Abstract
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)(C6F5)2BCHO was then isolated as a stable compound. This product underwent typical reactions of carbonyl compounds, such as Wittig olefination.
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