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Unique reactivity of an alpha-ketiminopyridine ligand with metal-alkyls: Synthesis and ROP of epsilon-caprolactone
Year: 2021
Type of publication: článek v odborném periodiku
Name of source: New Journal of Chemistry
Publisher name: Royal Society of Chemistry
Place: Cambridge
Page from-to: 3800-3808
Titles:
Language Name Abstract Keywords
cze Unikátní reaktivita alfa-ketiminopyridinového ligandu s alkyl-kovy: Syntéza a ROP epsilon-kaprolaktonu Alfa-ketimininopyridinový ligand 2-((Me)C=N(C6H3-2,6-iPr2))-6-(OMe)C5H3N (L1) byl studován v reakcích s alkyl-kovy, jako jsou MeLi, Et2Zn, Me3Al a Me2AlCl. Reakce ligandu L1 s MeLi vedla výhradně ke vzniku [2-((H2C)CN(C6H3-2,6-iPr2))-6-(OMe)C5H3N]Li·(THF)2 (1·(THF)2) s deprotonovanou methylovou skupinou ketiminu jako produktu eliminace metanu. Reakce ligandu L1 s Et2Zn poskytla v prvním stupni pouze komplex [2-((Me)C=N(C6H3-2,6-iPr2))-6-(OMe)C5H3N]ZnEt2 (2). Nestabilita sloučeniny 2 vedla k eliminaci etanu společně s deprotonací methylové skupiny ketiminu za poskytnutí [2-((H2C)CN(C6H3-2,6-iPr2))-6-(OMe)C5H3N]ZnEt (3). Naproti tomu, Me3Al reagoval s ligandem L1 karbaluminačním způsobem a byl izolován amid hlinitý [2-((Me)2C-N(C6H3-2,6-iPr2))-6-(OMe)C5H3N]AlMe2 (4). V případě reakce s Me2AlCl vznikl iontový komplex {[2-((Me)C=N(C6H3-2,6-iPr2))-6-(OMe)C5H3N]AlMe2}+{Me2AlCl2}-(5) jako produkt spontánní disociace Me2AlCl iniciované ligandem L1. Vzhledem k faktu, že sloučeniny 2-5 obsahují alkyl-kovový fragment, byly tyto sloučeniny použity jako katalyzátory v ROP -kaprolaktonu, stejně jako sloučenina 1·(THF)2. alfa-ketiminopyridin; alkyl-kov; ring-opening polymerace; epsilon-kaprolakton
eng Unique reactivity of an alpha-ketiminopyridine ligand with metal-alkyls: Synthesis and ROP of epsilon-caprolactone The reaction of an alpha-ketimininopyridine ligand 2-((Me)C = N(C6H3-2,6-iPr(2)))-6-(OMe)C5H3N (L-1) with metal-alkyls, such as MeLi, Et2Zn, Me3Al and Me2AlCl, was studied. The reaction of L-1 with MeLi led exclusively to the formation of [2-((H2C)C-N(C6H3-2,6-iPr(2)))-6-(OMe)C5H3N]Li center dot(THF)(2) (1 center dot(THF)(2)) with a deprotonated ketimine methyl group as a product of methane elimination. The treatment of L-1 with Et2Zn provided, at the first stage, only complex [2-((Me)C = N(C6H3-2,6-iPr(2)))-6-(OMe)C5H3N]ZnEt2 (2). The nonstability of 2 led to ethane elimination along with the deprotonation of a ketimine methyl group, which further yielded [2-((H2C)C-N(C6H3-2,6-iPr(2)))-6-(OMe)C5H3N]ZnEt (3). In contrast, Me3Al reacted with L-1 in a carboalumination fashion and [2-((Me)(2)C-N(C6H3-2,6-iPr(2)))-6-(OMe)C5H3N]AlMe2 (4) was isolated. In the case of Me2AlCl, an ionic species {[2-((Me)C = N(C6H3-2,6-iPr(2)))-6-(OMe)C5H3N]AlMe2}(+) {Me2AlCl2}(-) (5) was formed as a result of a spontaneous dissociation of Me2AlCl initiated by the ligand L-1. Since compounds 2-5 contain a metal-alkyl fragment, they were used as pre-catalysts in ROP of epsilon-caprolactone, as well as compound 1 center dot(THF)(2). epsilon-caprolactone; alpha-ketiminopyridine; alkyl-iron

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