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

Minyan Li, Simon Berritt, Carol Wang, Xiaodong Yang, Yang Liu, Sheng-Chun Sha, Bo Wang, Rui Wang, Xuyu Gao, Zhanyong Li, Xinyuan Fan, Youtian Tao and Patrick J. Walsh ()
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Minyan Li: University of Pennsylvania
Simon Berritt: University of Pennsylvania
Carol Wang: University of Pennsylvania
Xiaodong Yang: University of Pennsylvania
Yang Liu: University of Pennsylvania
Sheng-Chun Sha: University of Pennsylvania
Bo Wang: University of Pennsylvania
Rui Wang: Nanjing Tech University
Xuyu Gao: Nanjing Tech University
Zhanyong Li: Nankai University
Xinyuan Fan: Nanjing Tech University
Youtian Tao: Nanjing Tech University
Patrick J. Walsh: University of Pennsylvania

Nature Communications, 2018, vol. 9, issue 1, 1-9

Abstract: Abstract 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.

Date: 2018
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DOI: 10.1038/s41467-018-04095-x

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