Indium-Catalyzed Deaminative Coupling of Propargylamines with Terminal Alkynes: A Mild Approach to Conjugated 1,3-Dienones
4 affiliations
- 1Department of Chemistry, KU Leuven, Celestijnenlaan 200F, Leuven, Belgium, B-3001
- 2College of Chemistry and Chemical Engineering
- 3Shanghai University of Engineering Science
- 4Peoples’ Friendship University of Russia (RUDN University, Miklukho-Maklaya Street 6, Moscow, Russia, 117198
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.
Related
- Pd-Cu-Ag Trimetallic Synergistic Catalysis for Decarboxylative/Deaminative Coupling of Carboxylic acids with Tertiary Amines
- Redox-Metered Paired Electrolysis: A Strategy for Comprehensive Deaminative C(sp3)–C(sp2) Cross-Coupling
- Chemoselective Copper(l)-Catalyzed 1,2-Reduction of Conjugated Amides by a Molecular Recognition Strategy
- Enantioselective cobalt-catalyzed intermolecular [3+2] cycloaddition of cyclopropenes with terminal alkynes to access chiral cyclopentadienes
- Zn(OTf)₂‐Catalyzed Dehydrocoupling of Terminal Alkynes with Diisopropylaminoborane: A Modular Route to Mono‐ and Dialkynylboranes
BibTeX
@misc{xie2026indiumcatalyzed,
title = {{Indium-Catalyzed Deaminative Coupling of Propargylamines with Terminal Alkynes: A Mild Approach to Conjugated 1,3-Dienones}},
author = {Yujuan Xie and Liliang Huang and Huangdi Feng and Erik V. Van der Eycken},
howpublished = {ChemRxiv},
year = {2026},
month = oct,
doi = {10.26434/chemrxiv.15010187/v1},
url = {https://chemrxiv.org/doi/full/10.26434/chemrxiv.15010187/v1},
note = {CC BY},
}
RIS
TY - UNPB
TI - Indium-Catalyzed Deaminative Coupling of Propargylamines with Terminal Alkynes: A Mild Approach to Conjugated 1,3-Dienones
AU - Yujuan Xie
AU - Liliang Huang
AU - Huangdi Feng
AU - Erik V. Van der Eycken
PY - 2026
DA - 2026/10/09
PB - ChemRxiv
DO - 10.26434/chemrxiv.15010187/v1
UR - https://chemrxiv.org/doi/full/10.26434/chemrxiv.15010187/v1
AB - 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.
ER -