N-Heterocyclic Carbene-Based Group 4 Catalysts for the Terpolymerization of Cyclohexene Oxide and Cyclic Anhydrides with CO2

Suresh L., Zwettler K., Törnroos K.W., Le W., Marcolini B., Frache G., Le Roux E.

ACS Organic and Inorganic Au, vol. 5, n° 3, pp. 171-180, 2025

Abstract

A series of bis-phenolate saturated N-heterocyclic carbene (NHC) group 4 complexes ([κ<sup>3</sup>-O,C,O]-NHC)M(OiPr)Cl(THF) (M = Ti, 1; Zr, 2; Hf, 3) in the presence of [PPN]Cl as cocatalyst were investigated and showed high activity in the tandem terpolymerization of phthalic anhydride (PA), cyclohexene oxide (CHO) with CO<sub>2</sub>. The resultant terpolymers revealed a diblock pattern leading selectively to poly(ester-b-carbonate). Subsequently, other titanium complexes ([κ<sup>3</sup>-O,C,O]-NHC)TiX<sub>2</sub> bearing various coligands (X = Cl, 4; OiPr, 5; OAc, 6; OAc<sup>F</sup>, 7) also displayed high activity with a turnover frequency (TOF) up to 460 h<sup>-1</sup> that is comparable to 1. Using the same tandem approach, the nature of terpolymers was modulated with other mono- and tricyclic anhydrides alongside CHO with CO<sub>2</sub>. Intrigued by the high rates of PA conversion observed experimentally in terpolymerization, complexes 1-3 as well as benzannulated and unsaturated NHC analogues of complex 1 were investigated as a stand-alone reaction for the copolymerization of PA and CHO. Complex 1/[PPN]Cl displayed excellent catalytic activity (TOF ∼ 1600 h<sup>-1</sup>) and high selectivity (≥99%) toward polyesters comparable to other highly active heteronuclear (Al/K and Fe/K) catalysts and binary (salen)MX systems. Kinetic studies performed on complexes 1 and 3 determined activation barriers (E<sub>a</sub>) consistent with the observed catalytic trend, i.e., E<sub>a</sub>: Ti < Hf.

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FRACHE Gilles

Elemental and Molecular Analysis

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