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Reactivity of a Sterically Unencumbered α-Borylated Phosphorus Ylide towards Small Molecules

Radius, Michael 1; Sattler, Ewald 1; Berberich, Helga 1; Breher, Frank 1
1 Institut für Anorganische Chemie (AOC), Karlsruher Institut für Technologie (KIT)


The influence of substituents on α‐borylated phosphorus ylides (α‐BCPs) has been investigated in a combined experimental and quantum chemical approach. The synthesis and characterization of Me$_{3}$PC(H)B(iBu)$_{2}$ (1), consisting of small Me substituents on phosphorous and iBu residues on boron, is reported. Compound 1 is accessible through a novel synthetic approach, which has been further elucidated through DFT studies. The reactivity of 1 towards various small molecules was probed and compared with that of a previously published derivative, Ph$_{3}$PC(Me)BEt$_{2}$ (2). Both α‐BCPs react with NH$_{3}$ to undergo heterolytic N−H bond cleavage. Different di‐ and trimeric ring structures were observed in the reaction products of 1 with CO and CO$_{2}$. With PhNCO and PHNCS, the expected insertion products [Me$_{3}$PC(H)(PhNCO)B(iBu)$_{2}$] and [Me$_{3}$PC(H)(PhNCS)B(iBu)$_{2}$], respectively, were isolated.

Verlagsausgabe §
DOI: 10.5445/IR/1000098417
Veröffentlicht am 02.10.2019
DOI: 10.1002/chem.201902681
Zitationen: 10
Web of Science
Zitationen: 10
Zitationen: 10
Cover der Publikation
Zugehörige Institution(en) am KIT Institut für Anorganische Chemie (AOC)
Publikationstyp Zeitschriftenaufsatz
Publikationsjahr 2019
Sprache Englisch
Identifikator ISSN: 0947-6539, 1521-3765
KITopen-ID: 1000098417
Erschienen in Chemistry - a European journal
Verlag John Wiley and Sons
Band 25
Heft 52
Seiten 12206-12213
Nachgewiesen in Scopus
Web of Science
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