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Molecules 2018, 23(2), 360; https://doi.org/10.3390/molecules23020360

Chemoselective Polymerization of Polar Divinyl Monomers with Rare-Earth/Phosphine Lewis Pairs

1
,
1
,
1,2
and
1,*
1
Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, China
2
Suzhou International Academy, BFSU, Suzhou 215200, China
*
Author to whom correspondence should be addressed.
Received: 6 January 2018 / Revised: 1 February 2018 / Accepted: 6 February 2018 / Published: 8 February 2018
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Abstract

This work reports the chemoselective polymerization of polar divinyl monomers, including allyl methacrylate (AMA), vinyl methacrylate (VMA), and 4-vinylbenzyl methacrylate (VBMA), by using simple Lewis pairs comprised of homoleptic rare-earth (RE) aryloxide complexes RE(OAr)3 (RE = Sc (1), Y (2), Sm (3), La (4), Ar = 2,6-tBu2C6H3) and phosphines PR3 (R = Ph, Cy, Et, Me). Catalytic activities of polymerizations relied heavily upon the cooperation of Lewis acid and Lewis base components. The produced polymers were soluble in common organic solvents and often had a narrow molecular weight distribution. A highly syndiotactic poly(allyl methacrylate) (PAMA) with rr ~88% could be obtained by the scandium complex 1/PEt3 pair at −30 °C. In the case of poly(4-vinylbenzyl methacrylate) (PVBMA), it could be post-functionalized with PhCH2SH. Mechanistic study, including the isolation of the zwitterionic active species and the end-group analysis, revealed that the frustrated Lewis pair (FLP)-type addition was the initiating step in the polymerization. View Full-Text
Keywords: Lewis pairs; rare-earth; phosphines; chemoselective polymerization Lewis pairs; rare-earth; phosphines; chemoselective polymerization
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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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Xu, P.; Wu, L.; Dong, L.; Xu, X. Chemoselective Polymerization of Polar Divinyl Monomers with Rare-Earth/Phosphine Lewis Pairs. Molecules 2018, 23, 360.

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