Advances in Transition Metal-Catalyzed Carbonylation Reactions for α,β-Unsaturated Carbonyls: Applications, Challenges, and Opportunities

被引:0
作者
Mehara, Pushkar [1 ,2 ]
Sharma, Poonam [1 ,2 ]
Das, Pralay [1 ,2 ]
机构
[1] CSIR Inst Himalayan Bioresource Technol, Chem Technol Div, Palampur 176061, Himachal Prades, India
[2] Acad Sci & Innovat Res AcSIR, Ghaziabad 201002, India
关键词
heck reaction; C1; surrogate; hydroformylation; Pauson-Khand reaction; alpha; beta-unsaturated carbonyls; PAUSON-KHAND REACTION; ZWITTERIONIC RHODIUM COMPLEX; TERMINAL ALKYNES; REGIOSELECTIVE HYDROFORMYLATION; CARBOCYCLIZATION-CARBONYLATION; ARYL HALIDES; SELECTIVE SYNTHESIS; SUPPORTED RHODIUM; BOND FORMATION; HECK REACTION;
D O I
10.1002/tcr.202500071
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Over the past two decades, transition metal-catalyzed carbonylative reactions have revolutionized the synthesis of alpha,beta-unsaturated carbonyl compounds. These innovative, atom-economic transformations elegantly incorporate CO moiety into readily available substrates as well as complex molecules to produce a wide array of valuable compounds, including carboxylic acids, esters, ketones, amides, aldehydes, and cyclic carbonyls. These versatile products have immense applications in material science, pharmaceuticals, agrochemicals, and fine chemicals. This review aims to summarize and critically highlight the recent advancements in the carbonylation process for the synthesis of alpha,beta-unsaturated carbonyl compounds including a detailed description of mechanisms and comprehensive functional group compatibility. Additionally, the challenges in the relevant domain such as selectivity, catalyst efficiency, and scalability as well as exploring the exciting potential for its future development have been covered. We hope this review will serve as a convenient reference for the last 15 years in the field of carbonylation reactions for alpha,beta-unsaturated carbonyl compounds using a variety of transition metal catalysts and carbon monoxide (or its surrogates) as C1 source.
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页数:47
相关论文
共 185 条
[41]   AgBF4-Impregnated poly(vinyl phenyl ketone):: An ethylene sensing film [J].
Green, O ;
Smith, NA ;
Ellis, AB ;
Burstyn, JN .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (19) :5952-5953
[42]   Palladium catalysed reactions of allenes, carbon monoxide and nucleophiles. [J].
Grigg, R ;
Monteith, M ;
Sridharan, V ;
Terrier, C .
TETRAHEDRON, 1998, 54 (15) :3885-3894
[43]   Pd-catalysed carbonylations: versatile technology for discovery and process chemists [J].
Grigg, Ronald ;
Mutton, Simon P. .
TETRAHEDRON, 2010, 66 (30) :5515-5548
[44]   Supported Rhodium Nanoparticle-Catalyzed Intermolecular Regioselective Carbonylative Cyclization of Terminal Alkynes using Oxalic Acid as Sustainable C1 Source [J].
Guha, Nitul Ranjan ;
Thakur, Vandna ;
Bhattacherjee, Dhananjay ;
Bharti, Richa ;
Das, Pralay .
ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (23) :3743-3747
[45]   Rhodium-catalyzed highly regioselective hydroformylation-hydrogenation of 1,2-allenyl-phosphine oxides and -phosphonates [J].
Guo, Hao ;
Ma, Shengming .
ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (09) :1213-1217
[46]   Palladium-catalyzed carbonylation of aryl halides: an efficient, heterogeneous and phosphine-free catalytic system for aminocarbonylation and alkoxycarbonylation employing Mo(CO)6 as a solid carbon monoxide source [J].
Hajipour, Abdol-Reza ;
Tavangar-Rizi, Zeinab ;
Iranpoor, Nasser .
RSC ADVANCES, 2016, 6 (82) :78468-78476
[47]   PALLADIUM-CATALYZED VINYLIC HYDROGEN SUBSTITUTION REACTIONS WITH ARYL, BENZYL, AND STYRYL HALIDES [J].
HECK, RF ;
NOLLEY, JP .
JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (14) :2320-&
[48]   Carbonylative Heck Reactions Using CO Generated ex Situ in a Two-Chamber System [J].
Hermange, Philippe ;
Gogsig, Thomas M. ;
Lindhardt, Anders T. ;
Taaning, Rolf H. ;
Skrydstrup, Troels .
ORGANIC LETTERS, 2011, 13 (09) :2444-2447
[49]  
Hou J., 2015, ANGEW CHEM, V127, P6400, DOI [10.1002/ange.201501054, DOI 10.1002/ANGE.201501054]
[50]   Nickel-catalyzed hydrocarboxylation of alkynes with formic acid [J].
Hou, Jing ;
Yuan, Ming-Lei ;
Xie, Jian-Hua ;
Zhou, Qi-Lin .
GREEN CHEMISTRY, 2016, 18 (10) :2981-2984