Gold(I)-catalyzed addition of carboxylic acids to internal alkynes in aqueous medium

被引：25

作者：

Gonzalez-Liste, Pedro J. ^{[1
]}

Garcia-Garrido, Sergio E. ^{[1
]}

Cadierno, Victorio ^{[1
]}

机构：

[1] Univ Oviedo, Lab Comp Organomet & Catalisis, Ctr Innovac Quim Avanzada ORFEO CINQA, Unidad Asociada,CSIC,Dept Quim Organ & Inorgan,IU, E-33006 Oviedo, Spain

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2017年 / 15卷 / 07期

关键词：

ENOL ESTERS; GOLD CATALYSIS; TERMINAL ALKYNES; HIGHLY EFFICIENT; INTRAMOLECULAR CYCLIZATION; STEREOSELECTIVE ADDITION; SELECTIVE ADDITION; CYCLOISOMERIZATION; COMPLEXES; ACYLATION;

D O I：

10.1039/c6ob02800d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report herein the efficient hydro-oxycarbonylation of symmetrical and unsymmetrical internal alkynes with carboxylic acids in water at 60 degrees C, employing the catalytic system [AuCl(PPh3)]/AgOAc (5 mol%). This simple and eco-friendly protocol allows for the synthesis of a wide variety of trisubstituted enol esters (37 examples) in high yields and with complete Z-stereoselectivity. The use of microwave irradiation as an alternative energy source has also been evaluated.

引用

页码：1670 / 1679

页数：10

共 50 条

[41] Gold(I)-Catalyzed Enantioselective Carboalkoxylation of Alkynes
Zi, Weiwei
Toste, F. Dean
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (34) : 12600 - 12603
[42] Synthesis of Carbene-Metal-Amido (CMA) Complexes and Their Use as Precatalysts for the Activator-Free, Gold-Catalyzed Addition of Carboxylic Acids to Alkynes
Hashim, Ishfaq Ibni
Tzouras, Nikolaos, V
Janssens, Wim
Scattolin, Thomas
Bourda, Laurens
Bhandary, Subhrajyoti
Van Hecke, Kristof
Nolan, Steven P.
Cazin, Catherine S. J.
CHEMISTRY-A EUROPEAN JOURNAL, 2022, 28 (47)
[43] Amidation of polyaromatic carboxylic acids in aqueous medium
Maruyama, R
Ono, S
Inoue, M
TETRAHEDRON LETTERS, 2000, 41 (27) : 5229 - 5232
[44] Enol Ester Synthesis via Cobalt-Catalyzed Regio- and Stereoselective Addition of Carboxylic Acids to Alkynes
Chen, Jia-Feng
Li, Changkun
ORGANIC LETTERS, 2018, 20 (21) : 6719 - 6724
[45] Microwave-Assisted Synthesis of Vinyl Esters through Ruthenium-Catalyzed Addition of Carboxylic Acids to Alkynes
Nicks, Francois
Libert, Lionel
Delaude, Lionel
Demonceau, Albert
AUSTRALIAN JOURNAL OF CHEMISTRY, 2009, 62 (03) : 227 - 231
[46] Complexity-generating hydration reactions via gold-catalyzed addition of boronic acids to alkynes
Sheppard, Tom D.
PURE AND APPLIED CHEMISTRY, 2012, 84 (11) : 2431 - 2441
[47] Cobalt-Catalyzed Cross Addition of Silylacetylenes to Internal Alkynes
Sakurada, Tetsuya
Sugiyama, Yu-ki
Okamoto, Sentaro
JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (08): : 3583 - 3591
[48] Iron-Catalyzed Oxidative Cleavage of Olefins and Alkynes to Carboxylic Acids with Aqueous tert-Butyl Hydroperoxide
Shaikh, Tanveer Mahamadali
Hong, Fung-E
ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (09) : 1491 - 1496
[49] PLATINUM CATALYZED HYDROSILYLATION OF ALKYNES - COMPARISON OF RATES OF ADDITION OF TERMINAL OLEFINS TO INTERNAL ALKYNES
LEWIS, LN
SY, KG
DONAHUE, PE
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1992, 427 (02) : 165 - 172
[50] Gold(I) catalyzed water and methanol additions to alkynes
Cruz, Leticia
Hahn, Christine
Heuman, Crystal
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2011, 241

← 1 2 3 4 5 →