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Indium-Catalyzed Deaminative Coupling of Propargylamines with Terminal Alkynes: A Mild Approach to Conjugated 1,3-Dienones

Year: 2026

Type: preprint

Abstract: A mild and efficient indium-catalyzed coupling of propargylamines with terminal alkynes has been developed, affording a diverse array of conjugated 1,3-dienones in good to excellent yields. The reaction proceeds via in situ hydrolysis of propargylamines to generate the corresponding enones, followed by an indium(III)-promoted syn-selective alkyne insertion. Using InCl3 as the catalyst and DBU as the base, the protocol features broad functional-group tolerance and operates under mild conditions. Mechanistic investigations indicate that indium activation is crucial for facilitating the addition of alkynes to enones, enabling selective construction of conjugated 1,3-dienones frameworks. This transformation represents a rare example of indium-catalyzed C–C bond formation and provides a practical and versatile approach to structurally diverse 1,3-dienones from readily available propargylamine precursors.

Source: ChemRxiv

DOI: 10.26434/chemrxiv.15010187/v1

Authors: Yujuan Xie, Liliang Huang, Huangdi Feng, Erik V. Van der Eycken

Institutions: KU Leuven, Shanghai University of Engineering Science, Peoples' Friendship University of Russia

Language: English

Topic: Catalytic Alkyne Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: Natural Science Foundation of Shanghai, China Scholarship Council, RUDN University, National Key Research and Development Program of China

Awards: G1747327019, G3217073516

OpenAlex ID: W7221067657

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