|
Pomocí [[fosfiny|fosfinového]] ligandu [[SPhos]] lže množství potřebného katalyzátoru snížit až na 0,001 molárních procent.<ref>{{Citace periodika | autor1 = R. Martin | autor2 = S. L. Buchwald | titul = Palladium-Catalyzed Suzuki−Miyaura Cross-Coupling Reactions Employing Dialkylbiaryl Phosphine Ligands | periodikum = [[Accounts of Chemical Research]] | rok vydání = 2008 | strany = 1461–1473 | doi = 10.1021/ar800036s | pmid = 18620434}}</ref>
TDíkyDíky těmto vlastnostem je Suzukiova reakce často používaným syntetickým postupem.
== Využití ==
===Industrial applicationsV průmyslu ===
TheSuzukiova Suzukireakce couplingse reactionvyužívá isk průmyslové scalablesynéze andmeziproduktů cost-effectivepři forvýrobě useléčiv ina thečistých synthesis of intermediates for [[pharmaceuticals]] or [[fine chemicals]]chemikálií..<ref name="Rouhi - Industry">{{cite news|last=Rouhi|first=A. Maureen|title=Fine Chemicals|newspaper=C&EN|date=6 September 2004}}</ref> TheV minulosti Suzukijejí reactionvyužití wasomezovaly oncevysoké limitedceny bykatalyzátorů higha levelsšpatná ofdostupnost catalystboronových andkyselin. thePrůmyslovými limitedSuzukiovými availability of [[boronic acid]]s.reakcemi Replacementsse forvyrábí [[halides]]řada werebiologicky alsoaktivních foundlátek, increasingjako the number of coupling partners for the [[halide]] or [[pseudohalide]] as well. Scaled up reactions have been carried out in the synthesis of a number of important biological compounds such asje CI-1034, whichpři usedjehož avýrobě [[triflate]]se andpoužívá [[boronictriflát acid]]a couplingboronová partnerskyselina, whichkdy waspři run on anpoužití 80 kg kilogramreaktantů scaledosahuje with avýtěžnost 95 % yield.<ref name=AOC-231>{{cite journal|last1=Jacks1|first1=Thomas E.|last2=Belmont |first2=Daniel T. |last3= Briggs |first3=Christopher A. |last4=Horne |first4= Nicole M. |last5=Kanter |first5=Gerald D. |last6=Karrick |first6=Greg L. |last7= Krikke |first7=James J. |last8=McCabe |first8=Richard J. |last9=Mustakis |first0=Jason G. |last10=Nanninga |first10=Thomas N. |title=Development of a Scalable Process for CI-1034, an Endothelin Antagonist|journal=Organic Process Research & Development|date=1 March 2004|volume=8|issue=2|pages=201–212|doi=10.1021/op034104g}}</ref>
AnotherDalším examplepříkladem isje the coupling ofreakce 3-pyridylborane andpyridylboranu s 1-bromobrom-3-(methylsulfonyl)benzenebenzenem, thatkterou formedse anvytváří intermediatemeziprodukt, thatz něhož wasmůže usedbýt inzískána thelátka synthesiss účinky ofna a[[centrální potentialnervová centralsoustava|centrální nervousnervovou system agentsoustavu]]. ThePři couplingreakci reactionse tovytváří form the intermediate produced (278 kg kilograms) in aproduktu s 92.,5% yieldvýtěžností.<ref name="Carey and Sundberg">{{citeCitace monografie book|title titul = Advanced Organic Chemistry | url = https://archive.org/details/advancedorganicc00care_636 |url-access vydavatel =limited Springer |year rok vydání = 2007 |publisher strany =Springer 739–747 |pages doi =[https: 10.1002//archivetcr.org/details/advancedorganicc00care_636/page/n762201300001 739]–747| pmid = 23568378}}</ref><ref name="Rouhi - Industry" />
[[FileSoubor:CNS Intermediate Synthesis Suzuki.png|center|CNS Intermediate Synthesis Suzuki]]
SignificantVýznamných effortspokroků havebylo beendosaženo putpři intovývoji theheterogenních developmentkatalyzátorů ofSuzukiovy heterogeneous catalysts for the Suzuki CC reactionreakce, motivatedcož bymá thevyužití performance gains in the industrial processv průmyslu (eliminatingusnadňuje theoddělení catalystkatalyzátoru separationod fromsubstrátu); theukázalo substrate)se, andže recentlykatalýza ajednoatomovými heterogenními Pd singlekatalyzátory atomje hetereogeneousvhodnější catalystnež hashomogenní beenkatalýza shown to outperform the industry default homogeneouspomocí Pd(PPh<sub>3</sub>)<sub>4</sub> catalyst.<ref>{{citeCitace periodika journal| author1autor1 = Zupeng Chen, Zupeng| spoluautoři |author2= Vorobyeva, Evgeniya |author3= MitchellVorobyeva, Sharon |author4= FakoMitchell, Edvin |author5= OrtuñoFako, Manuel A. |author6= LópezOrtuño, Núria |author-link6=[[Núria López|author7= Collins]], Sean M. |author8= MidgleyCollins, Paul A. |author9=Midgley, Sylvia Richard, Sylvia |author10=Gianvito Vilé, Gianvito |author11=Javier Pérez-Ramírez, Javier| year= 2018| titletitul = A heterogeneous single-atom palladium catalyst surpassing homogeneous systems for Suzuki coupling | journalperiodikum = [[Nature Nanotechnology|]] volume = 13| issuerok = 8| pagesvydání = 702–7072018 | doistrany =10.1038/s41565-018-0167-2|pmid= 29941887702–707 | hdl=url 2072/359786|s2cid= 49415437 |url= http://eprints.whiterose.ac.uk/156636/1/s41565-018-0167-2.pdf | doi = 10.1038/s41565-018-0167-2 | pmid = 29941887}}</ref>
===Synthetic applicationsV laboratořích ===
Suzukiova reakce má využití při syntézách složitých organických struktur.<ref>{{Citace periodika | autor1 = Aaron Balog | autor2 = Dongfang Meng | autor3 = Ted Kamenecka | autor4 = Peter Bertinato | autor5 = Dai-Shi Su | autor6 = Erik J. Sorensen | autor7 = Samuel J. Danishefsky | titul = Total Synthesis of(–)-Epothilone A | periodikum = [[Angewandte Chemie|Angewandte Chemie International Edition in English]] | rok vydání = 1996 | strany = 2801–2803 | doi = 10.1002/anie.199628011}}</ref><ref>{{Citace periodika | autor1 = Junjia Liu | autor2 = Stephen D. Lotesta | autor3 = Erik J. Sorensen | titul = A concise synthesis of the molecular framework of pleuromutilin | periodikum = Chemical Communications | rok vydání = 2011 | strany = 1500–1502 | doi = 10.1039/C0CC04077K | pmid =21079876}}</ref>
The Suzuki coupling has been frequently used in syntheses of complex compounds.<ref>{{cite journal| doi =10.1002/anie.199628011| title =Total Synthesis of(–)-Epothilone A| year =1996| last1 =Balog| first1 =Aaron| last2 =Meng| first2 =Dongfang| last3 =Kamenecka| first3 =Ted| last4 =Bertinato| first4 =Peter| last5 =Su| first5 =Dai-Shi| last6 =Sorensen| first6 =Erik J.| last7 =Danishefsky| first7 =Samuel J.| journal =Angewandte Chemie International Edition in English| volume =35| issue =2324| pages =2801–2803}}</ref><ref>{{cite journal| doi =10.1039/C0CC04077K| title =A concise synthesis of the molecular framework of pleuromutilin| year =2011| last1 =Liu| first1 =Junjia| last2 =Lotesta| first2 =Stephen D.| last3 =Sorensen| first3 =Erik J.| journal =Chemical Communications| volume =47| issue =5| pages =1500–2| pmid =21079876| pmc =3156455}}</ref> The Suzuki coupling has been used on a [[citronellal]] derivative for the synthesis of [[caparratriene]], a natural product that is highly active against leukemia:<ref name=Vyvyan1999>{{cite journal | author = Vyvyan, J. R. | year = 1999 | title = An expedient total synthesis of (+/−)-caparratriene | journal = Tetrahedron Letters | volume = 40 | issue = 27 | pages = 4947–4949 | doi = 10.1016/S0040-4039(99)00865-5 | first2 = Emily A. | last3 = Stephan | first3 = Mari L.| last2 = Peterson}}</ref>
Suzukiova reakce byla použita na přípravu derivátu [[citronellal]]u, sloužícího jako meziprodukt přípravy kaparratrienu, látky aktivní proti leukémii:<ref>{{Citace periodika | autor1 = J. R. Vyvyan | autor2 = Emily A. Peterson | autor3 = Mari L. Stephan | titul = An expedient total synthesis of (+/−)-caparratriene | periodikum = [[Tetrahedron Letters]] | rok vydání = 1999 | strany = 4947–4949 | doi = 10.1016/S0040-4039(99)00865-5 | pmid =21079876}}</ref>
[[File:Suzuki coupling capparatriene.tif|frameless|center|720x157px]] ▼
▲[[ FileSoubor:Suzuki coupling capparatriene.tif|frameless|center| 720x157px700x200px]]
==Variations==
▲<!-- == ApplicationsVariations==
===Metal catalyst===
Various catalytic uses of metals other than palladium (especially nickel) have been developed.<ref name="Han - Nickel">{{cite journal|last=Han|first=Fu-She|title=Transition-metal-catalyzed Suzuki–Miyaura cross-coupling reactions: a remarkable advance from palladium to nickel catalysts|journal=Chemical Society Reviews|date=1 January 2013|volume=42|issue=12|pages=5270–98|doi=10.1039/c3cs35521g|pmid=23460083}}</ref> The first nickel catalyzed cross-coupling reaction was reported by Percec and co-workers in 1995 using aryl mesylates and boronic acids.<ref name=Percec1995>{{cite journal|last1=Percec|first1=Virgil|first2=Jin-Young |last2=Bae|first3=Dale |last3=Hill|title=Aryl Mesylates in Metal Catalyzed Homocoupling and Cross-Coupling Reactions. 2. Suzuki-Type Nickel-Catalyzed Cross-Coupling of Aryl Arenesulfonates and Aryl Mesylates with Arylboronic Acids|journal=Journal of Organic Chemistry|date=1995|volume=60|issue=4|pages=1060–1065|doi=10.1021/jo00109a044}}</ref> Even though a higher amount of nickel [[catalyst]] was needed for the reaction, around 5 mol %, [[nickel]] is not as expensive or as [[precious metal|precious]] a metal as [[palladium]]. The nickel catalyzed Suzuki coupling reaction also allowed a number of compounds that did not work or worked worse for the palladium catalyzed system than the nickel-catalyzed system.<ref name="Han - Nickel" /> The use of nickel catalysts has allowed for electrophiles that proved challenging for the original Suzuki coupling using palladium, including substrates such as phenols, aryl ethers, esters, phosphates, and fluorides.<ref name="Han - Nickel" />
| 