Sulfenate anions as organocatalysts for benzylic chloromethyl coupling polymerization via C=C bond formation

Organocatalytic polymerization reactions have a number of advantages over their metal-catalyzed counterparts, including environmental friendliness, ease of catalyst synthesis and storage, and alternative reaction pathways. Here we introduce an organocatalytic polymerization method called benzylic ch...

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Bibliographic Details
Published in:Nature communications 2018-05, Vol.9 (1), p.1754-9, Article 1754
Main Authors: Li, Minyan, Berritt, Simon, Wang, Carol, Yang, Xiaodong, Liu, Yang, Sha, Sheng-Chun, Wang, Bo, Wang, Rui, Gao, Xuyu, Li, Zhanyong, Fan, Xinyuan, Tao, Youtian, Walsh, Patrick J.
Format: Article
Language:English
Subjects:
140/131
639/638/403/933
639/638/455/941
639/638/455/954
639/638/77/889
Anions
Bonding
Chemical reactions
Chemical synthesis
Coupling
Humanities and Social Sciences
Intermediates
Metals
Monomers
multidisciplinary
Polymerization
Polymers
Science
Science (multidisciplinary)
Sulfoxides
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Summary:Organocatalytic polymerization reactions have a number of advantages over their metal-catalyzed counterparts, including environmental friendliness, ease of catalyst synthesis and storage, and alternative reaction pathways. Here we introduce an organocatalytic polymerization method called benzylic chloromethyl-coupling polymerization (BCCP). BCCP is catalyzed by organocatalysts not previously employed in polymerization processes (sulfenate anions), which are generated from bench-stable sulfoxide precatalysts. The sulfenate anion promotes an umpolung polycondensation via step-growth propagation cycles involving sulfoxide intermediates. BCCP represents an example of an organocatalyst that links monomers by C=C double bond formation and offers transition metal-free access to a wide variety of polymers that cannot be synthesized by traditional precursor routes. Polymerization reactions are often catalysed by metal compounds and hence there are concerns surrounding toxicity, cost and environmental friendliness. Here the authors show sulfenate anions as organocatalysts for benzylic chloromethyl-coupling polymerization reactions to form poly(stilbene)s.
ISSN:2041-1723
2041-1723
DOI:10.1038/s41467-018-04095-x