Cross-coupling reaction

{{Short description|Chemical reaction in which two molecules are joined due to a metal catalyst}}

In organic chemistry, a '''cross-coupling reaction''' is a reaction where two different fragments are joined. Cross-couplings are a subset of the more general coupling reactions. Often cross-coupling reactions require metal catalysts. One important reaction type is this: :<chem>R-M + R'X -> R-R' + MX</chem> ::R, R' = organic fragments, usually aryl; ::M = main group center such as Li or Mg; ::X = halide

These reactions are used to form carbon–carbon bonds but also carbon-heteroatom bonds.<ref>{{cite journal |doi=10.1021/acs.chemrev.8b00628 |title=Cross-Coupling of Heteroatomic Electrophiles |date=2019 |last1=Korch |first1=Katerina M. |last2=Watson |first2=Donald A. |journal=Chemical Reviews |volume=119 |issue=13 |pages=8192–8228 |pmid=31184483 |pmc=6620169 }}</ref><ref>{{cite journal |doi=10.1021/cr0505268 |title=Selected Patented Cross-Coupling Reaction Technologies |date=2006 |last1=Corbet |first1=Jean-Pierre |last2=Mignani |first2=Gérard |journal=Chemical Reviews |volume=106 |issue=7 |pages=2651–2710 |pmid=16836296 }}</ref><!--<ref>''Organic Synthesis using Transition Metals'' Rod Bates {{ISBN|978-1-84127-107-1}}</ref>--><ref>''New Trends in Cross-Coupling: Theory and Applications'' Thomas Colacot (Editor) 2014 {{ISBN|978-1-84973-896-5}}</ref><ref name=Pharma>{{cite book|author=King, A. O.|author2=Yasuda, N.|title=Organometallics in Process Chemistry|volume=6|pages=205–245 |chapter=Palladium-Catalyzed Cross-Coupling Reactions in the Synthesis of Pharmaceuticals|doi=10.1007/b94551|publisher = Springer|location=Heidelberg|series=Topics in Organometallic Chemistry|year=2004|isbn=978-3-540-01603-8}}</ref> Cross-coupling reaction are a subset of coupling reactions.

Richard F. Heck, Ei-ichi Negishi, and Akira Suzuki were awarded the 2010 Nobel Prize in Chemistry for developing palladium-catalyzed coupling reactions.<ref>{{cite web|url=https://nobelprize.org/nobel_prizes/chemistry/laureates/2010/ |title=The Nobel Prize in Chemistry 2010 - Richard F. Heck, Ei-ichi Negishi, Akira Suzuki |publisher=NobelPrize.org |date=2010-10-06 |access-date=2010-10-06}}</ref><ref>{{cite journal | doi = 10.1002/anie.201107017| pmid = 22573393| title = Palladium-Catalyzed Cross-Coupling: A Historical Contextual Perspective to the 2010 Nobel Prize| journal = Angewandte Chemie International Edition| volume = 51| issue = 21| pages = 5062–5085| year = 2012| last1 = Johansson Seechurn| first1 = Carin C. C.| last2 = Kitching| first2 = Matthew O.| last3 = Colacot| first3 = Thomas J.| last4 = Snieckus| first4 = Victor| s2cid = 20582425| url = https://durham-repository.worktribe.com/output/1323930}}</ref>

==Mechanism== Many mechanisms exist reflecting the myriad types of cross-couplings, including those that do not require metal catalysts.<ref>{{cite journal |doi=10.1021/cr400274j|title=Transition-Metal-Free Coupling Reactions |year=2014 |last1=Sun |first1=Chang-Liang |last2=Shi |first2=Zhang-Jie |journal=Chemical Reviews |volume=114 |issue=18 |pages=9219–9280 |pmid=25184859 }}</ref> Often, however, cross-coupling refers to a metal-catalyzed reaction of a nucleophilic partner with an electrophilic partner. [[Image:Katalysezyklus-Kumada-Kupplung.png|class=skin-invert-image|380px|center|thumb|Mechanism proposed for Kumada coupling (L = Ligand, Ar = Aryl).]] In such cases, the mechanism generally involves reductive elimination of R-R' from L_nMR(R') (L = spectator ligand). This intermediate L_nMR(R') is formed in a two-step process from a low valence precursor L_nM. The oxidative addition of an organic halide (RX) to L_nM gives L_nMR(X). Subsequently, the second partner undergoes transmetallation with a source of R'⁻. The final step is reductive elimination of the two coupling fragments to regenerate the catalyst and give the organic product. Unsaturated substrates, such as C(sp)−X and C(sp²)−X bonds, couple more easily, in part because they add readily to the catalyst.

===Catalysts=== [[File:Sonogashira coupling mechanism.png|class=skin-invert-image|thumb|320 px|center|Mechanism proposed for the Sonogashira coupling.]]

Catalysts are often based on palladium, which is frequently selected due to high functional group tolerance. Organopalladium compounds are generally stable towards water and air. Palladium catalysts can be problematic for the pharmaceutical industry, which faces extensive regulation regarding heavy metals. Many pharmaceutical chemists attempt to use coupling reactions early in production to minimize metal traces in the product.<ref>{{cite journal |url=https://pubs.acs.org/cen/coverstory/83/8336chiral3.html |title=Removing Impurities |last=Thayer |first=Ann |date=2005-09-05 |journal=Chemical & Engineering News |access-date=2015-12-11 }}</ref> Heterogeneous catalysts based on Pd are also well-developed.<ref>{{cite journal|author=Yin, L.|author2=Liebscher, J.|s2cid=36974481|title=Carbon−Carbon Coupling Reactions Catalyzed by Heterogeneous Palladium Catalysts|journal=Chemical Reviews|year=2007|volume=107|issue=1|pages=133–173|doi=10.1021/cr0505674|pmid=17212474}}</ref>

Alternatives to palladium cross-couplings became prevalent in the 2000s, with interest in non-precious and less toxic metals.<ref>{{Cite web |title=Activation of C–O and C–N Bonds Using Non-Precious-Metal Catalysis |url=https://pubs.acs.org/action/cookieAbsent |access-date=2026-04-14 |website=pubs.acs.org |doi=10.1021/acscatal.0c03334 |pmc=8049354 |pmid=33868770|last=Boit|first=T.|last2=Bulger|first2=A.|last3=Dander|first3=J.|last4=Garg|first4=N.}}</ref> Copper-based catalysts are especially useful for coupling involving heteroatom-C bonds.<ref>{{cite journal | doi = 10.1021/cr0505268| pmid = 16836296| title = Selected Patented Cross-Coupling Reaction Technologies| journal = Chemical Reviews| volume = 106| issue = 7| pages = 2651–2710| year = 2006| last1 = Corbet| first1 = Jean-Pierre| last2 = Mignani| first2 = Gérard}}</ref><ref>{{cite journal | doi = 10.1021/cr8002505| pmid = 18698737| title = Copper-Mediated Coupling Reactions and Their Applications in Natural Products and Designed Biomolecules Synthesis| journal = Chemical Reviews| volume = 108| issue = 8| pages = 3054–3131| year = 2008| last1 = Evano| first1 = Gwilherm| last2 = Blanchard| first2 = Nicolas| last3 = Toumi| first3 = Mathieu}}</ref> Iron-<ref>{{cite journal|title=How Low Does Iron Go? Chasing the Active Species in Fe-Catalyzed Cross-Coupling Reactions|author=Robin B. Bedford|journal=Acc. Chem. Res.|year=2015|volume=48|issue=5|pages=1485–1493|doi=10.1021/acs.accounts.5b00042|pmid=25916260}}</ref> and cobalt-catalysis have also been investigated.<ref>{{cite journal | doi = 10.1021/cr9000786| pmid = 20148539| title = Cobalt-Catalyzed Cross-Coupling Reactions| journal = Chemical Reviews| volume = 110| issue = 3| pages = 1435–1462| year = 2010| last1 = Cahiez| first1 = GéRard| last2 = Moyeux| first2 = Alban}}</ref> The use of nickel-based catalysis has become more widespread.<ref name=":0">{{cite journal | doi = 10.1021/cr100259t| pmid = 21133429| pmc = 3055945| title = Nickel-Catalyzed Cross-Couplings Involving Carbon−Oxygen Bonds| journal = Chemical Reviews| volume = 111| issue = 3| pages = 1346–1416| year = 2011| last1 = Rosen| first1 = Brad M.| last2 = Quasdorf| first2 = Kyle W.| last3 = Wilson| first3 = Daniella A.| last4 = Zhang| first4 = Na| last5 = Resmerita| first5 = Ana-Maria| last6 = Garg| first6 = Neil K.| last7 = Percec| first7 = Virgil}}</ref><ref>{{Cite journal |last=Tasker |first=Sarah Z. |last2=Standley |first2=Eric A. |last3=Jamison |first3=Timothy F. |date=May 2014 |title=Recent advances in homogeneous nickel catalysis |url=https://www.nature.com/articles/nature13274 |journal=Nature |language=en |volume=509 |issue=7500 |pages=299–309 |doi=10.1038/nature13274 |issn=1476-4687|pmc=4344729 }}</ref><ref>{{Cite journal |last=Baviskar |first=Bhushan A. |last2=Ajmire |first2=Prashant V. |last3=Chumbhale |first3=Deshraj S. |last4=Khan |first4=Mohammad Sadat |last5=Kuchake |first5=Vitthal G. |last6=Singupuram |first6=Madhavi |last7=Laddha |first7=Purushottam R. |date=2023-05-01 |title=Recent advances in nickel catalyzed Suzuki-Miyaura cross coupling reaction via C-O& C-N bond activation |url=https://www.sciencedirect.com/science/article/pii/S2352554122003576 |journal=Sustainable Chemistry and Pharmacy |volume=32 |article-number=100953 |doi=10.1016/j.scp.2022.100953 |issn=2352-5541|url-access=subscription }}</ref><ref>{{Cite web |title=Process-Ready Nickel-Catalyzed Suzuki–Miyaura Coupling Enabled by tri-ProPhos |url=https://pubs.acs.org/action/cookieAbsent |access-date=2026-04-14 |website=pubs.acs.org |doi=10.1021/acscatal.5c07157 |pmc=12645473 |pmid=41307039}}</ref><ref>{{Cite web |title=Nickel-Catalyzed Suzuki–Miyaura Couplings in Green Solvents |url=https://pubs.acs.org/action/cookieAbsent |access-date=2026-04-14 |website=pubs.acs.org |doi=10.1021/ol401727y |pmc=3768281 |pmid=23879392}}</ref>

===Leaving groups=== The leaving group X in the organic partner is usually a halide, although triflate, tosylate, pivalate esters,<ref>{{Cite journal |last=Quasdorf |first=Kyle W. |last2=Tian |first2=Xia |last3=Garg |first3=Neil K. |date=2008-11-05 |title=Cross-Coupling Reactions of Aryl Pivalates with Boronic Acids |journal=Journal of the American Chemical Society |volume=130 |issue=44 |pages=14422–14423 |doi=10.1021/ja806244b |issn=0002-7863}}</ref> carbamates,<ref>{{Cite journal |last=Quasdorf |first=Kyle |last2=Riener |first2=Michelle |last3=Petrova |first3=Krastina |last4=Garg |first4=Neil |title=Suzuki−Miyaura Coupling of Aryl Carbamates, Carbonates, and Sulfamates |url=https://pubs.acs.org/doi/abs/10.1021/ja906477r |journal=J. Am. Chem. Soc. |volume=131 |issue=49 |page=17748 |via=American Chemical Society}}</ref><ref>{{Cite journal |last=Mesganaw |first=Tehetena |last2=Silberstein |first2=Amanda L. |last3=Ramgren |first3=Stephen D. |last4=Nathel |first4=Noah F. Fine |last5=Hong |first5=Xin |last6=Liu |first6=Peng |last7=Garg |first7=Neil K. |date=2011-08-08 |title=Nickel-catalyzed amination of aryl carbamates and sequential site-selective cross-couplings |url=https://pubs.rsc.org/en/content/articlelanding/2011/sc/c1sc00230a |journal=Chemical Science |language=en |volume=2 |issue=9 |pages=1766–1771 |doi=10.1039/C1SC00230A |issn=2041-6539|pmc=6520651 }}</ref> and other pseudohalides have been used.<ref name=":0" /><ref>{{March6th|page=792}}</ref> Chloride is an ideal group due to the low cost of organochlorine compounds. Frequently, however, C–Cl bonds are too inert, and bromide or iodide leaving groups are required for acceptable rates. The main group metal in the organometallic partner is usually an electropositive element such as tin, zinc, silicon, or boron.

==Carbon–carbon cross-coupling== Many cross-couplings entail forming carbon–carbon bonds.

{|align="center" class="wikitable" !Reaction||Year ! colspan="2" align=left |Reactant A ! colspan="2" align=left |Reactant B||Catalyst||Remark |- |Cadiot–Chodkiewicz coupling||1957||RC≡CH||sp||RC≡CX||sp||Cu||requires base |- |Castro–Stephens coupling||1963||RC≡CH||sp||Ar-X || sp²||Cu|| |- |Corey–House synthesis||1967||R₂CuLi or RMgX|| sp³ |R-X||sp², sp³ | Cu |Cu-catalyzed version by Kochi, 1971 |- |Kumada coupling||1972||RMgBr||sp², sp³||R-X || sp²||Pd or Ni or Fe|| |- |Heck reaction||1972||alkene||sp²||Ar-X || sp²||Pd or Ni||requires base |- |Sonogashira coupling||1975||ArC≡CH||sp||R-X ||sp³ sp²||Pd and Cu||requires base |- |Negishi coupling||1977||R-Zn-X||sp³, sp², sp||R-X ||sp³ sp²||Pd or Ni|| |- |Stille cross coupling||1978||R-SnR₃||sp³, sp², sp||R-X ||sp³ sp²||Pd or Ni|| |- |Suzuki reaction||1979||R-B(OR)₂||sp²||R-X ||sp³ sp²||Pd or Ni||requires base |- |Murahashi coupling<ref>{{Cite journal|last1=Murahashi|first1=Shunichi|last2=Yamamura|first2=Masaaki|last3=Yanagisawa|first3=Kenichi|last4=Mita|first4=Nobuaki|last5=Kondo|first5=Kaoru|date=1979|title=Stereoselective synthesis of alkenes and alkenyl sulfides from alkenyl halides using palladium and ruthenium catalysts|journal=The Journal of Organic Chemistry|language=en|volume=44|issue=14|pages=2408–2417|doi=10.1021/jo01328a016|issn=0022-3263}}</ref> |1979 |R-Li |sp², sp³ |R-X |sp² |Pd or Ru | |- |Hiyama coupling||1988||R-SiR₃||sp²||R-X ||sp³ sp²||Pd||requires base |- |Fukuyama coupling||1998||R-Zn-I||sp³||RCO(SEt)||sp²||Pd or Ni||see Liebeskind–Srogl coupling, gives ketones |- |Liebeskind–Srogl coupling||2000||R-B(OR)₂||sp³, sp²||RCO(SEt) Ar-SMe||sp²||Pd ||requires CuTC, gives ketones |- |Cross dehydrogenative coupling||2004||R-H||sp, sp², sp³||R'-H ||sp, sp², sp³||Cu, Fe, Pd etc.||requires oxidant or dehydrogenation |- |Decarboxylative cross-coupling||2000s||R-CO₂H||sp²||R'-X||sp, sp²||Cu, Pd||Requires little-to-no base |}

The restrictions on carbon atom geometry mainly inhibit β-hydride elimination when complexed to the catalyst.<ref>Clayden, J.; Greeves, N.; Warren, S. ''Organic Chemistry'', 2nd ed.; Oxford UP: Oxford, U.K., 2012. pp.&nbsp;1069-1102.</ref>

==Carbon–heteroatom coupling== Many cross-couplings entail forming carbon–heteroatom bonds (heteroatom = S, N, O). A popular method is the Buchwald–Hartwig reaction:

{{NumBlk|:|center|500px|The Buchwald–Hartwig reaction|{{EquationRef|Eq.1}}}}

{|align="center" class="wikitable" !Reaction||Year ! colspan="2" align=left |Reactant A ! colspan="2" align=left |Reactant B||Catalyst||Remark |- |Ullmann-type reaction||1905 |ArO-MM, ArNH₂,RS-M,NC-M||sp³||Ar-X (X = OAr, N(H)Ar, SR, CN) || sp²||Cu|| |- |Buchwald–Hartwig reaction<ref>{{cite journal|author=Ruiz-Castillo, P.|author2=Buchwald, S. L.|title=Applications of Palladium-Catalyzed C–N Cross-Coupling Reactions |journal=Chemical Reviews |year=2016|volume=116|issue=19 |pages=12564–12649|doi=10.1021/acs.chemrev.6b00512|pmid=27689804 |pmc=5070552}}</ref>||1994||R₂N-H ||sp³||R-X||sp²||Pd|| N-C coupling,<br/>second generation free amine |- |Chan–Lam coupling<ref>{{cite book|chapter=Recent Advances in Chan–Lam Coupling Reaction: Copper-Promoted C–Heteroatom Bond Cross-Coupling Reactions with Boronic Acids and Derivatives|author=Jennifer X. Qiao|author2=Patrick Y.S. Lam|title=Boronic Acids: Preparation and Applications in Organic Synthesis, Medicine and Materials|pages=315–361|editor=Dennis G. Hall|year=2011|publisher=Wiley-VCH|doi=10.1002/9783527639328.ch6|isbn=978-3-527-63932-8}}</ref>||1998||Ar-B(OR)₂||sp²||Ar-NH₂ || sp²||Cu|| |- |}

==Miscellaneous reactions== Palladium-catalyzes the cross-coupling of aryl halides with fluorinated arene. The process is unusual in that it involves C–H functionalisation at an electron deficient arene.<ref>{{cite journal |author1=M. Lafrance |author2=C. N. Rowley |author3=T. K. Woo |author4=K. Fagnou | title = Catalytic Intermolecular Direct Arylation of Perfluorobenzenes | year = 2006 | journal = J. Am. Chem. Soc. | volume = 128 | issue = 27 | pages = 8754–8756 | doi = 10.1021/ja062509l | pmid = 16819868|bibcode=2006JAChS.128.8754L |citeseerx=10.1.1.631.607 }}</ref>

A new class of cross-couplings was discovered in 2015 by the research teams of Neil Garg and Ken Houk involving amides as coupling partners.<ref>{{Cite journal |last=Hie |first=Liana |last2=Fine Nathel |first2=Noah F. |last3=Shah |first3=Tejas K. |last4=Baker |first4=Emma L. |last5=Hong |first5=Xin |last6=Yang |first6=Yun-Fang |last7=Liu |first7=Peng |last8=Houk |first8=K. N. |last9=Garg |first9=Neil K. |title=Conversion of amides to esters by the nickel-catalysed activation of amide C–N bonds |url=https://www.nature.com/articles/nature14615 |journal=Nature |language=en |volume=524 |issue=7563 |pages=79–83 |doi=10.1038/nature14615 |issn=1476-4687|pmc=4529356 }}</ref> Nickel catalysis breaks the typical strong C-N bonds of amides through oxidative addition.<ref>{{Cite journal |last=Boit |first=Timothy B. |last2=Bulger |first2=Ana S. |last3=Dander |first3=Jacob E. |last4=Garg |first4=Neil K. |date=2020-10-16 |title=Activation of C–O and C–N Bonds Using Non-Precious-Metal Catalysis |url=https://doi.org/10.1021/acscatal.0c03334 |journal=ACS Catalysis |volume=10 |issue=20 |pages=12109–12126 |doi=10.1021/acscatal.0c03334 |pmc=8049354 |pmid=33868770}}</ref> Using nickel or palladium, transformations of amides can be achieved, including esterification, transamidation, hydrolysis, Suzuki-Miyaura couplings,<ref>{{Cite journal |last=Weires |first=Nicholas A. |last2=Baker |first2=Emma L. |last3=Garg |first3=Neil K. |title=Nickel-catalysed Suzuki–Miyaura coupling of amides |url=https://www.nature.com/articles/nchem.2388 |journal=Nature Chemistry |language=en |volume=8 |issue=1 |pages=75–79 |doi=10.1038/nchem.2388 |issn=1755-4349|url-access=subscription }}</ref> and asymmetric Heck reactions.<ref>{{Cite journal |last=Bulger |first=Ana S. |last2=Nasrallah |first2=Daniel J. |last3=Meza |first3=Arismel Tena |last4=Garg |first4=Neil K. |date=2024-02-14 |title=Enantioselective nickel-catalyzed Mizoroki–Heck cyclizations of amide electrophiles |url=https://pubs.rsc.org/en/content/articlelanding/2024/sc/d3sc05797f |journal=Chemical Science |language=en |volume=15 |issue=7 |pages=2593–2600 |doi=10.1039/D3SC05797F |issn=2041-6539}}</ref><ref>{{Cite web |last=Dander |first=J. |last2=Garg |first2=N. |title=Breaking Amides Using Nickel Catalysis |url=https://pubs.acs.org/action/cookieAbsent |access-date=2026-05-20 |website=pubs.acs.org |doi=10.1021/acscatal.6b03277 |pmc=5473294 |pmid=28626599}}</ref><ref>{{Cite journal |last=Meng |first=Guangrong |last2=Szostak |first2=Michal |date=2016-06-15 |title=Palladium-catalyzed Suzuki–Miyaura coupling of amides by carbon–nitrogen cleavage: general strategy for amide N–C bond activation |url=https://pubs.rsc.org/en/content/articlelanding/2016/ob/c6ob00084c |journal=Organic & Biomolecular Chemistry |language=en |volume=14 |issue=24 |pages=5690–5707 |doi=10.1039/C6OB00084C |issn=1477-0539|url-access=subscription }}</ref>

==Applications== Cross-coupling reactions are important for the production of pharmaceuticals,<ref name=Pharma/> examples being montelukast, eletriptan, naproxen, varenicline, and resveratrol.<ref>{{cite book|doi=10.1002/9783527651733.ch2|chapter=Hydroformylation|title=Applied Homogeneous Catalysis with Organometallic Compounds|year=2017|last1=Cornils|first1=Boy|last2=Börner|first2=Armin|last3=Franke|first3=Robert|last4=Zhang|first4=Baoxin|last5=Wiebus|first5=Ernst|last6=Schmid|first6=Klaus|pages=23–90|isbn=978-3-527-32897-0}}</ref> with Suzuki coupling being most widely used.<ref>{{cite journal |doi=10.1021/jm200187y|title=The Medicinal Chemist's Toolbox: An Analysis of Reactions Used in the Pursuit of Drug Candidates|year=2011|last1=Roughley|first1=Stephen D.|last2=Jordan|first2=Allan M.|journal=Journal of Medicinal Chemistry|volume=54|issue=10|pages=3451–3479|pmid=21504168}}</ref> Some polymers and monomers are also prepared in this way.<ref name=JFH>Hartwig, J. F. Organotransition Metal Chemistry, from Bonding to Catalysis; University Science Books: New York, 2010. {{ISBN|1-891389-53-X}}</ref>

== See also == * {{anl|Cross electrophile coupling}}

==Reviews== *{{Cite journal|title = N-Heterocyclic carbene (NHC) ligands and palladium in homogeneous cross-coupling catalysis: a perfect union|journal = Chemical Society Reviews|volume = 40|issue = 10|pages = 5151–69|doi = 10.1039/c1cs15088j|pmid = 21731956|language = en|first1 = George C.|last1 = Fortman|first2 = Steven P.|last2 = Nolan|year = 2011}} *{{cite journal | doi = 10.1021/cr0505674| pmid = 17212474| title = Carbon−Carbon Coupling Reactions Catalyzed by Heterogeneous Palladium Catalysts| journal = Chemical Reviews| volume = 107| issue = 1| pages = 133–173| year = 2007| last1 = Yin| last2 = Liebscher| first2 = Jürgen| s2cid = 36974481}} *{{cite journal | doi = 10.1021/cr100327p| pmid = 21319862| pmc = 3075866| title = Advances in Transition Metal (Pd,Ni,Fe)-Catalyzed Cross-Coupling Reactions Using Alkyl-organometallics as Reaction Partners| journal = Chemical Reviews| volume = 111| issue = 3| pages = 1417–1492| year = 2011| last1 = Jana| first1 = Ranjan| last2 = Pathak| first2 = Tejas P.| last3 = Sigman| first3 = Matthew S.}} *{{cite journal | doi = 10.1021/cr100355b| pmid = 21391571| title = Efficient, Selective, and Recyclable Palladium Catalysts in Carbon−Carbon Coupling Reactions| journal = Chemical Reviews| volume = 111| issue = 3| pages = 2251–2320| year = 2011| last1 = Molnár| first1 = Árpád}} *{{cite journal | doi = 10.1021/cr00039a007| title = Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds| journal = Chemical Reviews| volume = 95| issue = 7| pages = 2457–2483| year = 1995|author1-link=Norio Miyaura |author2-link=Akira Suzuki (chemist)| last1 = Miyaura| first1 = Norio| last2 = Suzuki| first2 = Akira| citeseerx = 10.1.1.735.7660}} *{{cite journal | doi = 10.1021/cr0509861| pmid = 17091930| title = Diazonium Salts as Substrates in Palladium-Catalyzed Cross-Coupling Reactions| journal = Chemical Reviews| volume = 106| issue = 11| pages = 4622–4643| year = 2006| last1 = Roglans| first1 = Anna| last2 = Pla-Quintana| first2 = Anna| last3 = Moreno-Mañas| first3 = Marcial| s2cid = 8128630}} *{{cite journal |doi=10.1021/acs.chemrev.8b00628|title=Cross-Coupling of Heteroatomic Electrophiles |year=2019 |last1=Korch |first1=Katerina M. |last2=Watson |first2=Donald A. |journal=Chemical Reviews |volume=119 |issue=13 |pages=8192–8228 |pmid=31184483 |pmc=6620169 }} *{{cite journal |doi=10.1021/cr9000786|title=Cobalt-Catalyzed Cross-Coupling Reactions |year=2010 |last1=Cahiez |first1=Gérard |last2=Moyeux |first2=Alban |journal=Chemical Reviews |volume=110 |issue=3 |pages=1435–1462 |pmid=20148539 }} *{{cite journal |doi=10.1021/acs.chemrev.6b00620|title=Recent Advances in Radical C–H Activation/Radical Cross-Coupling |year=2017 |last1=Yi |first1=Hong |last2=Zhang |first2=Guoting |last3=Wang |first3=Huamin |last4=Huang |first4=Zhiyuan |last5=Wang |first5=Jue |last6=Singh |first6=Atul K. |last7=Lei |first7=Aiwen |journal=Chemical Reviews |volume=117 |issue=13 |pages=9016–9085 |pmid=28639787 }}

==References== {{Reflist}} {{Organic reactions}} {{Authority control}}

{{DEFAULTSORT:Coupling Reaction}} Category:Coupling reactions Category:Organometallic chemistry Category:Carbon-carbon bond forming reactions Category:Catalysis