Pillar[n]arene-based phosphine ligands: synthesis, coordination chemistry and application in selective Au(I) catalysis

Article Article scientifique Article Pillar[n]arene-based phosphine ligands: synthesis, coordination chemistry and application in selective Au(I) catalysis eng 2026 author Konter Antoine Department of Organic Chemistry, University of Geneva 30 quai Ernest Ansermet 1211 Geneva Switzerland clement.mazet@unige.ch. 974991 author Buccio Michele Department of Organic Chemistry, University of Geneva 30 quai Ernest Ansermet 1211 Geneva Switzerland clement.mazet@unige.ch. 418655 Chimie organique (groupe 4) (CHOR4) author Vidal Louis Simon 0009-0008-9383-2311 Department of Organic Chemistry, University of Geneva 30 quai Ernest Ansermet 1211 Geneva Switzerland clement.mazet@unige.ch. 444364 Chimie organique (groupe 4) (CHOR4) author Besnard Céline 0000-0001-5699-9675 Laboratory of Crystallography, University of Geneva 24 quai Ernest Ansermet 1211 Geneva Switzerland. 682138 Administration de la section de chimie (CHIAD) author Mazet Clement 0000-0002-2385-280X Department of Organic Chemistry, University of Geneva 30 quai Ernest Ansermet 1211 Geneva Switzerland clement.mazet@unige.ch. 667534 Département de chimie organique (CHIOR) 5887-5897 10.1039/d6qo00815a 42516765 2052-4110 PMC13403166 http://pubs.rsc.org/QO/article-lookup/doi/10.1039/D6QO00815A We report a divergent and modular synthetic strategy for the functionalization of pillar[n ]arenes, enabling the synthesis of a comprehensive library of 17 mono- and bisphosphine ligands. By leveraging a Pd-catalyzed phosphinylation of A1/A2-ditriflate-pillararenes, we demonstrate that precise stoichiometric control permits the isolation of bifunctional phosphine-triflate intermediates. These scaffolds serve as versatile pivotal intermediates for the construction of rim-differentiated bisphosphines and hybrid aryl-phosphine derivatives via sequential Pd-catalyzed cross-couplings. Coordination studies with gold(i) precursors, supported by X-ray crystallography, reveal a certain degree of conformational plasticity inherent to the macrocyclic backbone. The catalytic utility of these macromolecular ligands was validated in the gold(i)-catalyzed cycloisomerization of 1,6-enynes, where several derivatives exhibited excellent levels of regioselectivity. Dewey 540 Swiss National Science Foundation Increasing molecular complexity by selective catalysis 188490 CH Swiss National Science Foundation Advancing transition metal selective catalysis 219276 CH 36 Département de chimie organique 141 false 763 Groupe Mazet Organic chemistry frontiers 13 17 fbb5f3ce-28a0-4fc7-93dd-33d27bd5c5cd Article (Published version) Public d6qo00815a.pdf 3517015 application/pdf CC BY-4.0 aa0d5003f425a0f4075fc9e22fb57a70fe776278989edf33f22e4eeef28a8610 b41c65a6-2408-41eb-8799-e188286bf31f Supplemental data Public d6qo00815a1_suppl.pdf 12445030 application/pdf CC BY-4.0 15ffcf005df6dbd5a82c8a8a434455fe5d81051d225e2d64bc6296c6adb9d18d Vignette Public m_d6qo00815a-ga.png 106376 image/png openAccess Faculté des sciences / Section de chimie et biochimie / Département de chimie organique

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Pillar[n]arene-based phosphine ligands: synthesis, coordination chemistry and application in selective Au(I) catalysis	Organic chemistry frontiers			2026	2	2

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Vidal, Louis Simon