Functionalization of Carbon Monoxide and tert ‐Butyl Nitrile by Intramolecular Proton Transfer in a Bis(Phosphido) Thorium Complex

Vilanova, Sean P.; del Rosal, Iker; Tarlton, Michael L.; Maron, Laurent; Walensky, Justin R.

doi:10.1002/ange.201810511

Title: Functionalization of Carbon Monoxide and tert ‐Butyl Nitrile by Intramolecular Proton Transfer in a Bis(Phosphido) Thorium Complex

Journal Article · Tue Nov 20 00:00:00 EST 2018 · Angewandte Chemie

DOI:https://doi.org/10.1002/ange.201810511· OSTI ID:1483011

Vilanova, Sean P. ^[1]; del Rosal, Iker ^[2]; Tarlton, Michael L. ^[1]; Maron, Laurent ^[2];

^[1]

Department of Chemistry University of Missouri Columbia MO 65211 USA
Universite de Toulouse CNRS INSA, UPS, CNRS, UMR, UMR 5215 LPCNO 135 Avenue de Rangueil 31077 Toulouse France

Abstract We report intramolecular proton transfer reactions to functionalize carbon monoxide and tert ‐butyl nitrile from a bis(phosphido) thorium complex. The reaction of (C ₅ Me ₅ ) ₂ Th[PH(Mes)] ₂ , Mes=2,4,6‐Me ₃ C ₆ H ₂ , with 1 atm of CO yields (C ₅ Me ₅ ) ₂ Th( κ ² ‐(O,O)‐OCH ₂ PMes‐C(O)PMes), in which one CO molecule is inserted into each thorium–phosphorus bond. Concomitant transfer of two protons, formerly coordinated to phosphorus, are now bound to one of the carbon atoms from one of the inserted CO molecules. DFT calculations were employed to determine the lowest energy pathway. With tert ‐butyl nitrile, ^t BuCN, only one nitrile inserts into a thorium–phosphorus bond, but the proton is transferred to nitrogen with one phosphido remaining unperturbed affording (C ₅ Me ₅ ) ₂ Th[PH(Mes)][ κ ² ‐(P,N)‐N(H)C(CMe ₃ )P(Mes)]. Surprisingly, reaction of this compound with KN(SiMe ₃ ) ₂ removes the proton bound to nitrogen, not phosphorus.

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Sponsoring Organization:: USDOE

OSTI ID:: 1483011

Journal Information:: Angewandte Chemie, Journal Name: Angewandte Chemie Vol. 130 Journal Issue: 51; ISSN 0044-8249

Publisher:: Wiley Blackwell (John Wiley & Sons)Copyright Statement

Country of Publication:: Germany

Language:: English

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