fbpx
Wikipedia

Cross-coupling reaction

October 18, 2023

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:

R−M + R'−X → R−R' + MX (R, R' = organic fragments, usually aryle; M = main group center such as Li or MgX; X = halide)

These reactions are used to form carbon–carbon bonds but also carbon-heteroatom bonds.[1][2][3] 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.[4][5]

Mechanism Edit

Many mechanisms exist reflecting the myriad types of cross-couplings, including those that do not require metal catalysts.[6] Often, however, cross-coupling refers to a metal-catalyzed reaction of a nucleophilic partner with an electrophilic partner.

 
Mechanism proposed for Kumada coupling (L = Ligand, Ar = Aryl).

In such cases, the mechanism generally involves reductive elimination of R-R' from LnMR(R') (L = spectator ligand). This intermediate LnMR(R') is formed in a two step process from a low valence precursor LnM. The oxidative addition of an organic halide (RX) to LnM gives LnMR(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 Edit

 
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.[7] Heterogeneous catalysts based on Pd are also well developed.[8]

Copper-based catalysts are also common, especially for coupling involving heteroatom-C bonds.[9][10]

Iron-,[11] cobalt-,[12] and nickel-based[13] catalysts have been investigated.

Leaving groups Edit

The leaving group X in the organic partner is usually a halide, although triflate, tosylate and other pseudohalide have been used. 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 usually is an electropositive element such as tin, zinc, silicon, or boron.

Carbon–carbon cross-coupling Edit

Many cross-couplings entail forming carbon–carbon bonds.

Reaction Year Reactant A 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[14] 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
(Li) Cross dehydrogenative coupling(CDC) 2004 R-H sp, sp2, sp3 R'-H sp, sp2, sp3 Cu, Fe, Pd etc requires oxidant or dehydrogenation

Carbon–heteroatom coupling Edit

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

 
The Buchwald–Hartwig reaction

 

 

 

 

(Eq.1)

Reaction Year Reactant A 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[15] 1994 R2N-H sp3 R-X sp2 Pd N-C coupling,
second generation free amine
Chan–Lam coupling[16] 1998 Ar-B(OR)2 sp2 Ar-NH2 sp2 Cu

Miscellaneous reactions Edit

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.[17]

 
Fluoroarene coupling

Applications Edit

Cross-coupling reactions are important for the production of pharmaceuticals,[3] examples being montelukast, eletriptan, naproxen, varenicline, and resveratrol.[18] with Suzuki coupling being most widely used.[19] Some polymers and monomers are also prepared in this way.[20]

Reviews Edit

  • Fortman, George C.; Nolan, Steven P. (2011). "N-Heterocyclic carbene (NHC) ligands and palladium in homogeneous cross-coupling catalysis: a perfect union". Chemical Society Reviews. 40 (10): 5151–69. doi:10.1039/c1cs15088j. PMID 21731956.
  • Yin; Liebscher, Jürgen (2007). "Carbon−Carbon Coupling Reactions Catalyzed by Heterogeneous Palladium Catalysts". Chemical Reviews. 107 (1): 133–173. doi:10.1021/cr0505674. PMID 17212474. S2CID 36974481.
  • Jana, Ranjan; Pathak, Tejas P.; Sigman, Matthew S. (2011). "Advances in Transition Metal (Pd,Ni,Fe)-Catalyzed Cross-Coupling Reactions Using Alkyl-organometallics as Reaction Partners". Chemical Reviews. 111 (3): 1417–1492. doi:10.1021/cr100327p. PMC 3075866. PMID 21319862.
  • Molnár, Árpád (2011). "Efficient, Selective, and Recyclable Palladium Catalysts in Carbon−Carbon Coupling Reactions". Chemical Reviews. 111 (3): 2251–2320. doi:10.1021/cr100355b. PMID 21391571.
  • Miyaura, Norio; Suzuki, Akira (1995). "Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds". Chemical Reviews. 95 (7): 2457–2483. CiteSeerX 10.1.1.735.7660. doi:10.1021/cr00039a007.
  • Roglans, Anna; Pla-Quintana, Anna; Moreno-Mañas, Marcial (2006). "Diazonium Salts as Substrates in Palladium-Catalyzed Cross-Coupling Reactions". Chemical Reviews. 106 (11): 4622–4643. doi:10.1021/cr0509861. PMID 17091930. S2CID 8128630.
  • Korch, Katerina M.; Watson, Donald A. (2019). "Cross-Coupling of Heteroatomic Electrophiles". Chemical Reviews. 119 (13): 8192–8228. doi:10.1021/acs.chemrev.8b00628. PMC 6620169. PMID 31184483.
  • Cahiez, Gérard; Moyeux, Alban (2010). "Cobalt-Catalyzed Cross-Coupling Reactions". Chemical Reviews. 110 (3): 1435–1462. doi:10.1021/cr9000786. PMID 20148539.
  • Yi, Hong; Zhang, Guoting; Wang, Huamin; Huang, Zhiyuan; Wang, Jue; Singh, Atul K.; Lei, Aiwen (2017). "Recent Advances in Radical C–H Activation/Radical Cross-Coupling". Chemical Reviews. 117 (13): 9016–9085. doi:10.1021/acs.chemrev.6b00620. PMID 28639787.

References Edit

  1. ^ Organic Synthesis using Transition Metals Rod Bates ISBN 978-1-84127-107-1
  2. ^ New Trends in Cross-Coupling: Theory and Applications Thomas Colacot (Editor) 2014 ISBN 978-1-84973-896-5
  3. ^ a b King, A. O.; Yasuda, N. (2004). "Palladium-Catalyzed Cross-Coupling Reactions in the Synthesis of Pharmaceuticals". Organometallics in Process Chemistry. Topics in Organometallic Chemistry. Vol. 6. Heidelberg: Springer. pp. 205–245. doi:10.1007/b94551. ISBN 978-3-540-01603-8.
  4. ^ "The Nobel Prize in Chemistry 2010 - Richard F. Heck, Ei-ichi Negishi, Akira Suzuki". NobelPrize.org. 2010-10-06. Retrieved 2010-10-06.
  5. ^ Johansson Seechurn, Carin C. C.; Kitching, Matthew O.; Colacot, Thomas J.; Snieckus, Victor (2012). "Palladium-Catalyzed Cross-Coupling: A Historical Contextual Perspective to the 2010 Nobel Prize". Angewandte Chemie International Edition. 51 (21): 5062–5085. doi:10.1002/anie.201107017. PMID 22573393. S2CID 20582425.
  6. ^ Sun, Chang-Liang; Shi, Zhang-Jie (2014). "Transition-Metal-Free Coupling Reactions". Chemical Reviews. 114 (18): 9219–9280. doi:10.1021/cr400274j. PMID 25184859.
  7. ^ Thayer, Ann (2005-09-05). "Removing Impurities". Chemical & Engineering News. Retrieved 2015-12-11.
  8. ^ Yin, L.; Liebscher, J. (2007). "Carbon−Carbon Coupling Reactions Catalyzed by Heterogeneous Palladium Catalysts". Chemical Reviews. 107 (1): 133–173. doi:10.1021/cr0505674. PMID 17212474. S2CID 36974481.
  9. ^ Corbet, Jean-Pierre; Mignani, Gérard (2006). "Selected Patented Cross-Coupling Reaction Technologies". Chemical Reviews. 106 (7): 2651–2710. doi:10.1021/cr0505268. PMID 16836296.
  10. ^ Evano, Gwilherm; Blanchard, Nicolas; Toumi, Mathieu (2008). "Copper-Mediated Coupling Reactions and Their Applications in Natural Products and Designed Biomolecules Synthesis". Chemical Reviews. 108 (8): 3054–3131. doi:10.1021/cr8002505. PMID 18698737.
  11. ^ Robin B. Bedford (2015). "How Low Does Iron Go? Chasing the Active Species in Fe-Catalyzed Cross-Coupling Reactions". Acc. Chem. Res. 48 (5): 1485–1493. doi:10.1021/acs.accounts.5b00042. PMID 25916260.
  12. ^ Cahiez, GéRard; Moyeux, Alban (2010). "Cobalt-Catalyzed Cross-Coupling Reactions". Chemical Reviews. 110 (3): 1435–1462. doi:10.1021/cr9000786. PMID 20148539.
  13. ^ Rosen, Brad M.; Quasdorf, Kyle W.; Wilson, Daniella A.; Zhang, Na; Resmerita, Ana-Maria; Garg, Neil K.; Percec, Virgil (2011). "Nickel-Catalyzed Cross-Couplings Involving Carbon−Oxygen Bonds". Chemical Reviews. 111 (3): 1346–1416. doi:10.1021/cr100259t. PMC 3055945. PMID 21133429.
  14. ^ Murahashi, Shunichi; Yamamura, Masaaki; Yanagisawa, Kenichi; Mita, Nobuaki; Kondo, Kaoru (1979). "Stereoselective synthesis of alkenes and alkenyl sulfides from alkenyl halides using palladium and ruthenium catalysts". The Journal of Organic Chemistry. 44 (14): 2408–2417. doi:10.1021/jo01328a016. ISSN 0022-3263.
  15. ^ Ruiz-Castillo, P.; Buchwald, S. L. (2016). "Applications of Palladium-Catalyzed C–N Cross-Coupling Reactions". Chemical Reviews. 116 (19): 12564–12649. doi:10.1021/acs.chemrev.6b00512. PMC 5070552. PMID 27689804.
  16. ^ Jennifer X. Qiao; Patrick Y.S. Lam (2011). "Recent Advances in Chan–Lam Coupling Reaction: Copper-Promoted C–Heteroatom Bond Cross-Coupling Reactions with Boronic Acids and Derivatives". In Dennis G. Hall (ed.). Boronic Acids: Preparation and Applications in Organic Synthesis, Medicine and Materials. Wiley-VCH. pp. 315–361. doi:10.1002/9783527639328.ch6. ISBN 9783527639328.
  17. ^ M. Lafrance; C. N. Rowley; T. K. Woo; K. Fagnou (2006). "Catalytic Intermolecular Direct Arylation of Perfluorobenzenes". J. Am. Chem. Soc. 128 (27): 8754–8756. CiteSeerX 10.1.1.631.607. doi:10.1021/ja062509l. PMID 16819868.
  18. ^ Cornils, Boy; Börner, Armin; Franke, Robert; Zhang, Baoxin; Wiebus, Ernst; Schmid, Klaus (2017). "Hydroformylation". Applied Homogeneous Catalysis with Organometallic Compounds. pp. 23–90. doi:10.1002/9783527651733.ch2. ISBN 9783527328970.
  19. ^ Roughley, Stephen D.; Jordan, Allan M. (2011). "The Medicinal Chemist's Toolbox: An Analysis of Reactions Used in the Pursuit of Drug Candidates". Journal of Medicinal Chemistry. 54 (10): 3451–3479. doi:10.1021/jm200187y. PMID 21504168.
  20. ^ Hartwig, J. F. Organotransition Metal Chemistry, from Bonding to Catalysis; University Science Books: New York, 2010. ISBN 1-891389-53-X

October 18, 2023
cross, coupling, reaction, organic, chemistry, cross, coupling, reaction, reaction, where, different, fragments, joined, cross, couplings, subset, more, general, coupling, reactions, often, cross, coupling, reactions, require, metal, catalysts, important, reac. 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 R M R X R R MX R R organic fragments usually aryle M main group center such as Li or MgX X halide These reactions are used to form carbon carbon bonds but also carbon heteroatom bonds 1 2 3 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 4 5 Contents 1 Mechanism 1 1 Catalysts 1 2 Leaving groups 2 Carbon carbon cross coupling 3 Carbon heteroatom coupling 4 Miscellaneous reactions 5 Applications 6 Reviews 7 ReferencesMechanism EditMany mechanisms exist reflecting the myriad types of cross couplings including those that do not require metal catalysts 6 Often however cross coupling refers to a metal catalyzed reaction of a nucleophilic partner with an electrophilic partner nbsp Mechanism proposed for Kumada coupling L Ligand Ar Aryl In such cases the mechanism generally involves reductive elimination of R R from LnMR R L spectator ligand This intermediate LnMR R is formed in a two step process from a low valence precursor LnM The oxidative addition of an organic halide RX to LnM gives LnMR 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 Edit nbsp 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 7 Heterogeneous catalysts based on Pd are also well developed 8 Copper based catalysts are also common especially for coupling involving heteroatom C bonds 9 10 Iron 11 cobalt 12 and nickel based 13 catalysts have been investigated Leaving groups Edit The leaving group X in the organic partner is usually a halide although triflate tosylate and other pseudohalide have been used 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 usually is an electropositive element such as tin zinc silicon or boron Carbon carbon cross coupling EditMany cross couplings entail forming carbon carbon bonds Reaction Year Reactant A Reactant B Catalyst RemarkCadiot Chodkiewicz coupling 1957 RC CH sp RC CX sp Cu requires baseCastro Stephens coupling 1963 RC CH sp Ar X sp2 CuCorey House synthesis 1967 R2CuLi or RMgX sp3 R X sp2 sp3 Cu Cu catalyzed version by Kochi 1971Kumada coupling 1972 RMgBr sp2 sp3 R X sp2 Pd or Ni or FeHeck reaction 1972 alkene sp2 Ar X sp2 Pd or Ni requires baseSonogashira coupling 1975 ArC CH sp R X sp3 sp2 Pd and Cu requires baseNegishi coupling 1977 R Zn X sp3 sp2 sp R X sp3 sp2 Pd or NiStille cross coupling 1978 R SnR3 sp3 sp2 sp R X sp3 sp2 Pd or NiSuzuki reaction 1979 R B OR 2 sp2 R X sp3 sp2 Pd or Ni requires baseMurahashi coupling 14 1979 R Li sp2 sp3 R X sp2 Pd or RuHiyama coupling 1988 R SiR3 sp2 R X sp3 sp2 Pd requires baseFukuyama coupling 1998 R Zn I sp3 RCO SEt sp2 Pd or Ni see Liebeskind Srogl coupling gives ketonesLiebeskind Srogl coupling 2000 R B OR 2 sp3 sp2 RCO SEt Ar SMe sp2 Pd requires CuTC gives ketones Li Cross dehydrogenative coupling CDC 2004 R H sp sp2 sp3 R H sp sp2 sp3 Cu Fe Pd etc requires oxidant or dehydrogenationCarbon heteroatom coupling EditMany cross couplings entail forming carbon heteroatom bonds heteroatom S N O A popular method is the Buchwald Hartwig reaction nbsp The Buchwald Hartwig reaction Eq 1 Reaction Year Reactant A Reactant B Catalyst RemarkUllmann type reaction 1905 ArO MM ArNH2 RS M NC M sp3 Ar X X OAr N H Ar SR CN sp2 CuBuchwald Hartwig reaction 15 1994 R2N H sp3 R X sp2 Pd N C coupling second generation free amineChan Lam coupling 16 1998 Ar B OR 2 sp2 Ar NH2 sp2 CuMiscellaneous reactions EditPalladium 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 17 nbsp Fluoroarene couplingApplications EditCross coupling reactions are important for the production of pharmaceuticals 3 examples being montelukast eletriptan naproxen varenicline and resveratrol 18 with Suzuki coupling being most widely used 19 Some polymers and monomers are also prepared in this way 20 Reviews EditFortman George C Nolan Steven P 2011 N Heterocyclic carbene NHC ligands and palladium in homogeneous cross coupling catalysis a perfect union Chemical Society Reviews 40 10 5151 69 doi 10 1039 c1cs15088j PMID 21731956 Yin Liebscher Jurgen 2007 Carbon Carbon Coupling Reactions Catalyzed by Heterogeneous Palladium Catalysts Chemical Reviews 107 1 133 173 doi 10 1021 cr0505674 PMID 17212474 S2CID 36974481 Jana Ranjan Pathak Tejas P Sigman Matthew S 2011 Advances in Transition Metal Pd Ni Fe Catalyzed Cross Coupling Reactions Using Alkyl organometallics as Reaction Partners Chemical Reviews 111 3 1417 1492 doi 10 1021 cr100327p PMC 3075866 PMID 21319862 Molnar Arpad 2011 Efficient Selective and Recyclable Palladium Catalysts in Carbon Carbon Coupling Reactions Chemical Reviews 111 3 2251 2320 doi 10 1021 cr100355b PMID 21391571 Miyaura Norio Suzuki Akira 1995 Palladium Catalyzed Cross Coupling Reactions of Organoboron Compounds Chemical Reviews 95 7 2457 2483 CiteSeerX 10 1 1 735 7660 doi 10 1021 cr00039a007 Roglans Anna Pla Quintana Anna Moreno Manas Marcial 2006 Diazonium Salts as Substrates in Palladium Catalyzed Cross Coupling Reactions Chemical Reviews 106 11 4622 4643 doi 10 1021 cr0509861 PMID 17091930 S2CID 8128630 Korch Katerina M Watson Donald A 2019 Cross Coupling of Heteroatomic Electrophiles Chemical Reviews 119 13 8192 8228 doi 10 1021 acs chemrev 8b00628 PMC 6620169 PMID 31184483 Cahiez Gerard Moyeux Alban 2010 Cobalt Catalyzed Cross Coupling Reactions Chemical Reviews 110 3 1435 1462 doi 10 1021 cr9000786 PMID 20148539 Yi Hong Zhang Guoting Wang Huamin Huang Zhiyuan Wang Jue Singh Atul K Lei Aiwen 2017 Recent Advances in Radical C H Activation Radical Cross Coupling Chemical Reviews 117 13 9016 9085 doi 10 1021 acs chemrev 6b00620 PMID 28639787 References Edit Organic Synthesis using Transition Metals Rod Bates ISBN 978 1 84127 107 1 New Trends in Cross Coupling Theory and Applications Thomas Colacot Editor 2014 ISBN 978 1 84973 896 5 a b King A O Yasuda N 2004 Palladium Catalyzed Cross Coupling Reactions in the Synthesis of Pharmaceuticals Organometallics in Process Chemistry Topics in Organometallic Chemistry Vol 6 Heidelberg Springer pp 205 245 doi 10 1007 b94551 ISBN 978 3 540 01603 8 The Nobel Prize in Chemistry 2010 Richard F Heck Ei ichi Negishi Akira Suzuki NobelPrize org 2010 10 06 Retrieved 2010 10 06 Johansson Seechurn Carin C C Kitching Matthew O Colacot Thomas J Snieckus Victor 2012 Palladium Catalyzed Cross Coupling A Historical Contextual Perspective to the 2010 Nobel Prize Angewandte Chemie International Edition 51 21 5062 5085 doi 10 1002 anie 201107017 PMID 22573393 S2CID 20582425 Sun Chang Liang Shi Zhang Jie 2014 Transition Metal Free Coupling Reactions Chemical Reviews 114 18 9219 9280 doi 10 1021 cr400274j PMID 25184859 Thayer Ann 2005 09 05 Removing Impurities Chemical amp Engineering News Retrieved 2015 12 11 Yin L Liebscher J 2007 Carbon Carbon Coupling Reactions Catalyzed by Heterogeneous Palladium Catalysts Chemical Reviews 107 1 133 173 doi 10 1021 cr0505674 PMID 17212474 S2CID 36974481 Corbet Jean Pierre Mignani Gerard 2006 Selected Patented Cross Coupling Reaction Technologies Chemical Reviews 106 7 2651 2710 doi 10 1021 cr0505268 PMID 16836296 Evano Gwilherm Blanchard Nicolas Toumi Mathieu 2008 Copper Mediated Coupling Reactions and Their Applications in Natural Products and Designed Biomolecules Synthesis Chemical Reviews 108 8 3054 3131 doi 10 1021 cr8002505 PMID 18698737 Robin B Bedford 2015 How Low Does Iron Go Chasing the Active Species in Fe Catalyzed Cross Coupling Reactions Acc Chem Res 48 5 1485 1493 doi 10 1021 acs accounts 5b00042 PMID 25916260 Cahiez GeRard Moyeux Alban 2010 Cobalt Catalyzed Cross Coupling Reactions Chemical Reviews 110 3 1435 1462 doi 10 1021 cr9000786 PMID 20148539 Rosen Brad M Quasdorf Kyle W Wilson Daniella A Zhang Na Resmerita Ana Maria Garg Neil K Percec Virgil 2011 Nickel Catalyzed Cross Couplings Involving Carbon Oxygen Bonds Chemical Reviews 111 3 1346 1416 doi 10 1021 cr100259t PMC 3055945 PMID 21133429 Murahashi Shunichi Yamamura Masaaki Yanagisawa Kenichi Mita Nobuaki Kondo Kaoru 1979 Stereoselective synthesis of alkenes and alkenyl sulfides from alkenyl halides using palladium and ruthenium catalysts The Journal of Organic Chemistry 44 14 2408 2417 doi 10 1021 jo01328a016 ISSN 0022 3263 Ruiz Castillo P Buchwald S L 2016 Applications of Palladium Catalyzed C N Cross Coupling Reactions Chemical Reviews 116 19 12564 12649 doi 10 1021 acs chemrev 6b00512 PMC 5070552 PMID 27689804 Jennifer X Qiao Patrick Y S Lam 2011 Recent Advances in Chan Lam Coupling Reaction Copper Promoted C Heteroatom Bond Cross Coupling Reactions with Boronic Acids and Derivatives In Dennis G Hall ed Boronic Acids Preparation and Applications in Organic Synthesis Medicine and Materials Wiley VCH pp 315 361 doi 10 1002 9783527639328 ch6 ISBN 9783527639328 M Lafrance C N Rowley T K Woo K Fagnou 2006 Catalytic Intermolecular Direct Arylation of Perfluorobenzenes J Am Chem Soc 128 27 8754 8756 CiteSeerX 10 1 1 631 607 doi 10 1021 ja062509l PMID 16819868 Cornils Boy Borner Armin Franke Robert Zhang Baoxin Wiebus Ernst Schmid Klaus 2017 Hydroformylation Applied Homogeneous Catalysis with Organometallic Compounds pp 23 90 doi 10 1002 9783527651733 ch2 ISBN 9783527328970 Roughley Stephen D Jordan Allan M 2011 The Medicinal Chemist s Toolbox An Analysis of Reactions Used in the Pursuit of Drug Candidates Journal of Medicinal Chemistry 54 10 3451 3479 doi 10 1021 jm200187y PMID 21504168 Hartwig J F Organotransition Metal Chemistry from Bonding to Catalysis University Science Books New York 2010 ISBN 1 891389 53 X Retrieved from https en wikipedia org w index php title Cross coupling reaction amp oldid 1179952646, wikipedia, wiki, book, books, library,

article

, read, download, free, free download, mp3, video, mp4, 3gp, jpg, jpeg, gif, png, picture, music, song, movie, book, game, games.