Recent Advances in the Transition Metal-Catalyzed Addition of Carboxylic Acids to Alkynes

被引:7
作者
Cadierno, Vittorio [1 ]
机构
[1] Univ Oviedo, Fac Quim, Dept Quim Organ & Inorgan, E-33006 Oviedo, Spain
关键词
Enol esters; lactones; alkynes; hydro-oxycarbonylation reactions; cycloisomerization reactions; metal-catalyzed transformations; ONE-POT SYNTHESIS; ANTI-MARKOVNIKOV ADDITION; CARBON-DIOXIDE INCORPORATION; O-DIENYL ESTERS; TERMINAL ALKYNES; ENOL ESTERS; ASYMMETRIC HYDROFORMYLATION; STEREOSELECTIVE ADDITION; EFFICIENT SYNTHESIS; SELECTIVE ADDITION;
D O I
10.2174/1385272825666210308113837
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Recent advances in the metal-catalyzed hydrofunctionalization of alkynes with carboxylic acids are comprehensively reviewed. Both inter- and intramolecular processes, leading respectively to enol esters and lactones, are discussed, as well as the involvement of these transformations in the synthesis of natural products and biologically active molecules, and the assembly of elaborated heterocyclic compounds through cascade processes. Literature published since 2011 is covered.
引用
收藏
页码:2260 / 2303
页数:44
相关论文
共 205 条
[41]   Early Steps of Homogeneous Catalysis in Rennes: Carbon Dioxide Incorporation, Alkyne Activation and Ruthenium Catalysis [J].
Dixneuf, Pierre H. .
CATALYSIS LETTERS, 2015, 145 (01) :360-372
[42]   GENERAL-SYNTHESIS OF (Z)-ALK-1-EN-1-YL ESTERS VIA RUTHENIUM-CATALYZED ANTI-MARKOVNIKOV TRANS-ADDITION OF CARBOXYLIC-ACIDS TO TERMINAL ALKYNES [J].
DOUCET, H ;
MARTINVACA, B ;
BRUNEAU, C ;
DIXNEUF, PH .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (22) :7247-7255
[43]   Carboxylic Acids as Directing Groups for C-H Bond Functionalization [J].
Drapeau, Martin Pichette ;
Goossen, Lukas J. .
CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (52) :18654-18677
[44]   Cyclisation of acetylenic carboxylic acids and acetylenic alcohols to oxygen-containing heterocycles using cationic rhodium(I) complexes [J].
Elgafi, S ;
Field, LD ;
Messerle, BA .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2000, 607 (1-2) :97-104
[45]   Enhanced Catalytic Performance of Indenediide Palladium Pincer Complexes for Cycloisomerization: Efficient Synthesis of Alkylidene Lactams [J].
Espinosa-Jalapa, Noel Angel ;
Ke, Diandian ;
Nebra, Noel ;
Le Goanvic, Lucas ;
Mallet-Ladeira, Sonia ;
Monot, Julien ;
Martin-Vaca, Blanca ;
Bourissou, Didier .
ACS CATALYSIS, 2014, 4 (10) :3605-3611
[46]   POLAR ADDITIONS TO OLEFINS AND ACTYLENES .3. KINETICS AND STEREOCHEMISTRY OF ADDITION IN SYSTEM 1-PHENYLPROPYNE-HYDROGEN CHLORIDE-ACETIC ACID [J].
FAHEY, RC ;
LEE, DJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1966, 88 (23) :5555-&
[47]   Silver-catalysed reactions of alkynes: recent advances [J].
Fang, Guichun ;
Bi, Xihe .
CHEMICAL SOCIETY REVIEWS, 2015, 44 (22) :8124-8173
[48]   Cu(I) Camphor Coordination Polymers: Synthesis and Study of the Catalytic Activity for Cyclization of 4-Pentyn-1-oic Acid [J].
Fernandes, Tiago A. ;
Galvao, Adelino M. ;
Botelho do Rego, Ana M. ;
Carvalho, M. Fernanda N. N. .
JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2014, 52 (23) :3316-3323
[49]   Condensation Oligomers with Sequence Control but without Coupling Reagents and Protecting Groups via Asymmetric Hydroformylation and Hydroacyloxylation [J].
Foarta, Floriana ;
Landis, Clark R. .
JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (22) :11250-11255
[50]   Catalytic Addition of Indole-2-Carboxylic Acid to 1-Hexyne [J].
Francos, Javier ;
Diaz-Alvarez, Alba E. ;
Cadierno, Victorio .
MOLBANK, 2020, 2020 (03) :1-6