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Inorganics 2018, 6(1), 28; https://doi.org/10.3390/inorganics6010028

Probing the Effect of Six-Membered N-Heterocyclic Carbene—6-Mes—on the Synthesis, Structure and Reactivity of Me2MOR(NHC) (M = Ga, In) Complexes

1
Centre of New Technologies, University of Warsaw, Banacha 2c, 02-097 Warsaw, Poland
2
Faculty of Chemistry, University of Warsaw, Pasteura 1, 02-093 Warsaw, Poland
3
Faculty of Chemistry, Warsaw University of Technology, Noakowskiego 3, 00-664, Warsaw, Poland
*
Author to whom correspondence should be addressed.
Received: 3 January 2018 / Revised: 31 January 2018 / Accepted: 12 February 2018 / Published: 16 February 2018
(This article belongs to the Special Issue N-Heterocyclic Carbene Metal Complexes: From Design to Applications)
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Abstract

The investigation of the reactivity of six membered N-heterocyclic carbene 1,3-bis(2,4,6-trimethylphenyl)-3,4,5,6-tetrahydropyrimidin-1-ylidene (6-Mes) towards dialkylgallium and dialkylindium alkoxides/aryloxides has shown that both steric hindrances and donor properties of 6-Mes significantly influence the strength of M–C6-Mes bond, as well as the formation, structure and reactivity of Me2MOR(6-Mes) (M = Ga, In) complexes. While the reactions of simple dimethylgallium alkoxides with 6-Mes lead to the formation of stable monomeric Me2Ga(OCH2CH2OMe)(6-Mes) (1) and Me2GaOMe(6-Mes) complexes, the analogous Me2InOR(6-Mes) are unstable and disproportionate to methylindium alkoxides and Me3In(6-Mes) (2). The use of bulky alkoxide ligand—OCPh2Me or aryloxide ligand—OC6H4OMe allowed for the synthesis of stable Me2M(OCPh2Me)(6-Mes) (M = Ga (3) and In (4)) as well as Me2M(OC6H4OMe)(6-Mes) (M = Ga (5) and In (6)). The structures of 16 have been determined using both spectroscopic methods in solution and X-ray diffraction studies, which confirmed the effect of both steric hindrances and donor properties of 6-Mes on their structure and catalytic properties in the ring-opening polymerization (ROP) of rac-lactide. View Full-Text
Keywords: metal alkoxides; main group metals; NHC donor strength; catalyst; lactide; stereoselectivity; isotactic polylactide metal alkoxides; main group metals; NHC donor strength; catalyst; lactide; stereoselectivity; isotactic polylactide
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Cybularczyk-Cecotka, M.; Dąbrowska, A.M.; Guńka, P.A.; Horeglad, P. Probing the Effect of Six-Membered N-Heterocyclic Carbene—6-Mes—on the Synthesis, Structure and Reactivity of Me2MOR(NHC) (M = Ga, In) Complexes. Inorganics 2018, 6, 28.

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