Editing Heck reaction (section)

==History==
The original reaction by Tsutomu Mizoroki (1971) describes the coupling between [[iodobenzene]] and [[styrene]] in [[methanol]] to form [[stilbene]] at 120&nbsp;°C ([[autoclave]]) with [[potassium acetate]] base and [[palladium chloride]] catalysis. This work was an extension of earlier work by Fujiwara (1967) on the Pd(II)-mediated coupling of arenes (Ar–H) and alkenes<ref>{{cite journal|last=Moritani|first=Ichiro|author2=Fujiwara, Yuzo|title=Aromatic substitution of styrene-palladium chloride complex|journal=[[Tetrahedron Lett.]]|year=1967|volume=8|issue=12|pages=1119–1122|doi=10.1016/S0040-4039(00)90648-8}}</ref><ref>{{cite journal|doi=10.1021/ja01053a047|title=Aromatic substitution of olefins. VI. Arylation of olefins with palladium(II) acetate|year=1969|last1=Fujiwara|first1=Yuzo|last2=Noritani|first2=Ichiro|last3=Danno|first3=Sadao|last4=Asano|first4=Ryuzo|last5=Teranishi|first5=Shiichiro|journal=[[J. Am. Chem. Soc.]]|volume=91|pages=7166–9|issue=25|pmid=27462934}}</ref> and earlier work by Heck (1969) on the coupling of arylmercuric halides (ArHgCl) with alkenes using a stoichiometric amount of a palladium(II) species.<ref>{{cite journal|doi=10.1021/ja01052a029|title=Mechanism of Arylation and Carbomethoxylation of Olefins with Organopalladium Compounds|year=1969|author= Richard F. Heck|author-link=Richard F. Heck|journal=J. Am. Chem. Soc.|volume=91|pages=6707–6714|issue=24}}</ref>

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[[File:Mizoroki 1971 iodobenzene styrene.svg|center|400px|Mizoroki 1971]]
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! Mizoroki 1971
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In 1972 Heck acknowledged the Mizoroki publication and detailed ''independently discovered'' work. Heck's reaction conditions differ in terms of the catalyst (palladium acetate), catalyst loading (0.01 eq.), base (hindered amine), and absence of solvent.<ref>{{cite journal | title = Palladium-catalyzed vinylic hydrogen substitution reactions with aryl, benzyl, and styryl halides | author1 = Heck, R. F.| author1-link = Richard F. Heck | author2 = Nolley, J. P. | journal = [[J. Org. Chem.]] | year = 1972 | volume = 37 | pages = 2320–2322 | doi = 10.1021/jo00979a024 | issue=14 }}</ref><ref>{{cite journal |author1=Mizoroki, T. |author2=Mori, K. |author3=Ozaki, A. | journal = [[Bull. Chem. Soc. Jpn.]] | year = 1971 | volume = 44 | pages = 581 | doi = 10.1246/bcsj.44.581 | title = Arylation of Olefin with Aryl Iodide Catalyzed by Palladium | issue = 2| doi-access =  }}</ref>

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[[File:Heck 1972 iodobenzene styrene.svg|center|400px|Heck 1972]]
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! Heck 1972
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In 1974 Heck showed that phosphine ligands facilitated the reaction.<ref>{{cite journal|doi=10.1021/ja00811a029|title=Organophosphinepalladium complexes as catalysts for vinylic hydrogen substitution reactions|year=1974|last1=Dieck|first1=H. A.|last2=Heck|first2=R. F.|journal=J. Am. Chem. Soc.|volume=96|pages=1133|issue=4}}</ref>
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[[File:Heck Dieck 1974.svg|center|400px|Dieck & Heck 1974]]
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! Heck reaction 1974 phosphines
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