Suzuki-Miyaura Cross-Coupling Reaction

Suzuki-Miyaura reaction is a palladium catalyzed cross-coupling reaction between organic boron compounds and organic halides.¹⁾ The reaction requires an additional base for the activation of the boron compound and proceeds under mild conditions. This relatively simple and versatile C-C bond formation reaction can be extended to various substrates and therefore finds wide application for the synthesis of pharmaceuticals and total synthesis of complex natural products.

The usefulness of this reaction has been well documented by the synthesis of biaryl compounds in 1981,²⁾ triggered by the initial synthesis of dienes using the vinyl-type boron compounds initiated in 1979.³⁾ Eventually the reaction also proved applicable to the coupling reaction of alkyl halides and alkylboranes. Organotrifluoroborates also represent an effective alternative to boronic acids and boronate esters being stable towards numerous reagents and allow the manipulation of functional groups within them.⁴⁾
N-Heterocyclic carbenes prepared from imidazolium and imidazolinium salts can also be efficiently employed as ligands in addition to organophosphine compounds.⁵⁾ Recently, the synthesis of biaryl compounds without the aid of ligands has also been accomplished.⁶⁾
It has been recently reported that nickel can also catalyze the above reaction with the same efficiency as the expensive palladium catalysts specially in case of difficult substrates like aryl chlorides in which reaction does not proceed easily with conventional palladium as the catalyst. In addition to being inexpensive, nickel catalysts can also be removed much easily from the reaction system.⁷⁾
Proper choice of metals, ligands, bases and solvents enable the widespread application of the Suzuki-Miyaura cross-coupling reaction to various substrates and different synthetic sequences.
We provide a wide range of organic boron compounds as coupling partners. We offer different varieties of reaction partners in addition to the organoboron compounds, such as metal catalysts and phosphine ligands to explore the versatile applicability of the Suzuki-Miyaura cross-coupling reaction.

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Product Brochure

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Product Category Pages

• Cross-coupling Reaction using Transition Metal Catalysts
  • Palladium Catalysts [Cross-coupling Reaction using Transition Metal Catalysts]
  • Nickel Catalysts [Cross-coupling Reaction using Transition Metal Catalysts]
  • Phosphine Ligands [Cross-coupling Reaction using Transition Metal Catalysts]
  • N-Heterocyclic Carbene (NHC) Ligands [Cross-coupling Reaction using Transition Metal Catalysts]
  • Bases and Additives [Cross-coupling Reaction using Transition Metal Catalysts]
  • Pyridinesulfinates, Pyrimidinesulfinates [Cross-coupling Reaction using Transition Metal Catalysts]
• Organoboron
  • Boronic Acids [Organoboron]
  • Boronate Esters [Organoboron]
  • Trifluoroborate Salts [Organoboron]

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Topics

• TCI Practical Example: Suzuki-Miyaura Coupling Using Ni(COD)₂
• TCI Practical Example: Suzuki-Miyaura Cross Coupling with PdCl₂(Amphos)₂
• TCI Practical Example: Suzuki-Miyaura Coupling of Diaminonaphthalene (dan)-Protected Bromophenylboronic Acid
• TCI Practical Example: Suzuki-Miyaura Cross Coupling Using an Alkenyl Boronic Acid Ester as a Substrate
• Palladium Catalyst for the Suzuki-Miyaura Coupling of Heteroaryl Chlorides
• New Palladacycle Precatalyst
• Useful Palladium Catalyst
• A Unique and Efficient Ni Catalyst for Cross-Coupling Reactions
• Pincer-type Nickel Catalyst
• Suzuki-Miyaura Cross Coupling Catalyzed by Cost-Effective Nickel Salt
• Bidendate Carbene Ligands Forming Various Transition Metal Complexes
• Silanol Salt for Deprotection Reactions and Cross-coupling Reactions
• Boronic Acid Derivative for the Synthesis of Diarylacetylenes
• Denitrogenative Suzuki-Miyaura Cross-coupling Reactions of benzotriazoles
• A Useful Methylene Unit Usable for Suzuki-Miyaura Cross-coupling
• Reagent for the Synthesis of gem-Disubstituted Cyclopropanes
• Efficient Trifluoroborates Usable for Introducing Methoxymethyl and Aminomethyl Groups
• Organotrifluoroborates for Cross-coupling leading to Hydroxymethylarenes and Aminomethylarenes
• Cross-coupling Reactions Using Organosodium

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References

• 1) Review:
  • a) A. Suzuki, Chem. Commun. 2005, 4759.
  • b) A. Suzuki, Yuki Gosei Kagaku Kyokaishi (J. Synth. Org. Chem., Jpn.) 2005, 63, 312.
  • c) A. Suzuki, Proc. Jpn. Acad., Ser. B 2004, 80, 359.
  • d) N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457.
  • e) A. J. J. Lennox, G. C. Lloyd-Jones, Chem. Soc. Rev. 2014, 43, 412.
• 2) N. Miyaura, K. Yamada, A. Suzuki, Tetrahedron Lett. 1979, 20, 3437.
• 3) T. Yanagi, N. Miyaura, A. Suzuki, Synth. Commun. 1981, 11, 513.
• 4) Review: G. A. Molander, N. Ellis, Acc. Chem. Res. 2007, 40, 275.
• 5) Review: E. A. B. Kantchev, C. J. O'Brien, M. G. Organ, Angew. Chem. Int. Ed. 2007, 46, 2768.
• 6) T. Maegawa, Y. Kitamura, S. Sako, T. Udzu, A. Sakurai, A. Tanaka, Y. Kobayashi, K. Endo, U. Bora, T. Kurita, A. Kozaki, Y. Monguchi, H. Sajiki, Chem. Eur. J. 2007, 13, 5937.
• 7) Review: T. Kamikawa, Fain Kemikaru 2006, 35, 53.

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