Copper-Catalyzed C(3+1) Copolymerization of Propargyl Carbonates and Aryldiazomethanes

02 December 2022, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

Controlling the composition and sequence during diazo copolymerization with vinyl or acetylenic monomers is challenging. Here we disclose a Cu-catalyzed C(3+1) copolymerization reaction using propargyl carbonates and aryldiazomethanes derived from N-tosylhydrazones as the C3 and C1 building blocks, respectively. This reaction rapidly produces alternating-like poly(1,4-diaryl-2-butyne-1,4-diyl)s (Mn up to 31.0 kg/mol) in a modular fashion, without detectable homopolymer segments. This work provides a new strategy for the synthesis of hydrocarbon polymers through diazo copolymerization.

Keywords

copper
diazo
propargyl carbonates
C1 polymerization
cumulenes

Supplementary materials

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Description
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supporting information
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NMR spectra, GPC traces, procedures, additional data
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