Shape Selectivity in the Gold-Catalyzed Hydration of Alkynes Using a Cavity-Shaped Phosphine

被引：5

作者：

Navarro, Miquel ^{[1
,2
,3
]}

Holzapfel, Markus ^{[1
,2
,3
,4
]}

Campos, Jesus ^{[1
,2
,3
]}

机构：

[1] Univ Seville, Inst Invest Quim IIQ, Dept Quim Inorgan, Ave Amer Vespucio 49, Seville 41092, Spain

[2] Univ Seville, Ctr Innovac Quim Avanzada ORFEO CINQA, Ave Amer Vespucio 49, Seville 41092, Spain

[3] CSIC, Ave Amer Vespucio 49, Seville 41092, Spain

[4] IMC Univ Appl Sci, Inst Appl Chem, Dept Sci & Technol, A-3500 Krems, Austria

来源：

CHEMPLUSCHEM | 2023年 / 88卷 / 07期

基金：

欧洲研究理事会;

关键词：

Alkynes; gold; homogeneous catalysis; hydration; phosphines; ACID-FREE CONDITIONS; ELIMINATION; REACTIVITY; SOLVENT;

D O I：

10.1002/cplu.202300231

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A cavity-shaped gold(I) complex derived from a bulky tri-(ortho-biaryl)-phosphine ligand shows preferred selectivity towards terminal functionalities in the gold(I)-catalysed hydration of alkynes under mild heating due to a well-defined pocket as catalytic active site. The confinement-induced size-exclusion selectivity investigated for eight alkynes contrasts with other gold(I) complexes bearing bulky phosphine ligands that show reduced selectivity or even similar behaviour towards both internal and terminal alkynes. We also interrogate the potential of gold(III) derivatives for the same catalytic process.

引用

页数：7

共 60 条

[21] Synthesis of Cyclobutene-Fused Eight-Membered Carbocycles through Gold-Catalyzed Intramolecular Enyne [2+2] Cycloaddition [J].

Iwai, Tomohiro ;

Ueno, Masahiro ;

Okochi, Hiori ;

Sawamura, Masaya .

ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (04) :670-675

[22] Construction of Eight-Membered Carbocycles through Gold Catalysis with Acetylene-Tethered Silyl Enol Ethers [J].

Iwai, Tomohiro ;

Okochi, Hiori ;

Ito, Hideto ;

Sawamura, Masaya .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (15) :4239-4242

[23] Phosphonium Formation by Facile Carbon Phosphorus Reductive Elimination from Gold(III) [J].

Kawai, Hiroyuki ;

Wolf, William J. ;

DiPasquale, Antonio G. ;

Winston, Matthew S. ;

Toste, F. Dean .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (02) :587-593

[24] One-pot syntheses of sterically shielded phosphorus ligands by selective stepwise nucleophilic substitution at triphenyl phosphite [J].

Keller, J ;

Schlierf, C ;

Nolte, C ;

Mayer, P ;

Straub, BF .

SYNTHESIS-STUTTGART, 2006, 2 (02) :354-365

[25] Gold-Catalyzed Nucleophilic Cyclization of Functionalized Allenes: A Powerful Access to Carbo- and Heterocycles [J].

Krause, Norbert ;

Winter, Christian .

CHEMICAL REVIEWS, 2011, 111 (03) :1994-2009

[26]

Kronig S., 2012, Angew. Chem, V124, P3294, DOI [10.1002/ange.201108813, DOI 10.1002/ANGE.201108813]

[27] Gold-Catalyzed Intermolecular Alkyne Hydrofunctionalizations-Mechanistic Insights [J].

Leung, Chin Hin ;

Baron, Marco ;

Biffis, Andrea .

CATALYSTS, 2020, 10 (10) :1-35

[28] Synthesis, Structure and Nickel Carbonyl Complexes of Dialkylterphenyl Phosphines [J].

Marin, Mario ;

Moreno, Juan J. ;

Navarro-Gilabert, Carlos ;

Alvarez, Eleuterio ;

Maya, Celia ;

Peloso, Riccardo ;

Carmen Nicasio, M. ;

Carmona, Ernesto .

CHEMISTRY-A EUROPEAN JOURNAL, 2019, 25 (01) :260-272

[29] Enantioselective Alkoxycyclization of 1,6-Enynes with Gold(I)-Cavitands: Total Synthesis of Mafaicheenamine C [J].

Martin-Torres, Inmaculada ;

Ogalla, Gala ;

Yang, Jin-Ming ;

Rinaldi, Antonia ;

Echavarren, Antonio M. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (17) :9339-9344

[30] Confinement-Induced Selectivities in Gold(I) Catalysis-The Benefit of Using Bulky Tri-(ortho-biaryl)phosphine Ligands [J].

Muratov, Karim ;

Gagosz, Fabien .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (28)

← 1 2 3 4 5 6 →