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Copper-Catalyzed Formal Dehydration Polymerization of Propargylic Alcohols via Cumulene Intermediates.

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Here we report a copper-catalyzed formal dehydration polymerization of propargylic alcohols. Copper catalysis allows for efficient in situ generation of [n]cumulenes (n = 3, 5) by a soft deprotonation/β-elimination pathway… Click to show full abstract

Here we report a copper-catalyzed formal dehydration polymerization of propargylic alcohols. Copper catalysis allows for efficient in situ generation of [n]cumulenes (n = 3, 5) by a soft deprotonation/β-elimination pathway and subsequent polymerization via organocopper species. Alkyne polymers (Mn up to 36.2 kg/mol) were produced with high efficiency (up to 95% yield) and excellent functional group tolerance. One-pot synthesis of semiconducting head-to-head poly(phenylacetylene) was demonstrated through a polymerization-isomerization sequence.

Keywords: copper catalyzed; polymerization propargylic; dehydration polymerization; polymerization; formal dehydration; catalyzed formal

Journal Title: Journal of the American Chemical Society
Year Published: 2022

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