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Suzuki reaction

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Rinshana Fathima

The Suzuki reaction is a palladium-catalyzed cross-coupling reaction between boronic acids or esters with organic halides, triflates, or other boron-containing compounds. This reaction occurs under basic conditions and leads to the formation of carbon-carbon single bonds, typically between an aryl or vinyl group and another aryl or vinyl group. It is commonly used to synthesize biaryl compounds. The reaction proceeds through oxidative addition, transmetallation, and reductive elimination steps. Key advantages are mild reaction conditions and availability of boronic acids. The Suzuki reaction has applications in synthesizing pharmaceuticals, agrochemicals, and natural products.

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SUZUKI REACTION SUZUKI MIYAURA REACTION SUZUKI COUPLING REACTION SUBMITTED BY : RINSHANA FATHIMA ABDUL AZEEZ FIRST YEAR M.PHARM PHARMACEUTICAL CHEMISTRY AL SHIFA COLLEGE OF PHARMACY 1
Suzuki reaction is the Pd catalysed cross coupling reaction[1] between the boronic / organoboronic acids / organoboranes with organic halides[2], triflates, etc under basic conditions[3] which leads to the formation of carbon carbon single bonds.[4] This reaction is commonly used for synthesising biaryl compounds. 2
GENERAL SCHEME 3
STEP 1 - Oxidative Addition - 2 groups adds to the metal. 4 MECHANISM
STEP 2 - Hydroxide attacks Pd, kicking off X 5
STEP 3 - Lewis base (OH鐚) attacks Lewis acid (B) 6 The Organo Boron has only 3 bonds around it and it is sp2 hybrised with an empty p orbital, making it a very good lewis acid.
STEP 4 - Transmetallation. Carbon will attach to a metal that has an electronegativity closer to it. Electronegativity Values C = 2.5 B = 2.0 Pd = 2.4
STEP 5 - Reductive Elimination - 2 groups are removed from a metal. 8
ADVANTAGES Mild reaction conditions. (From 20-80) Commercial availability of many boronic acids. The inorganic by-products are easily removed from the reaction mixture, making the reaction suitable for industrial processes 9
Generally aryl halides react sluggishly. By-products such as self-coupling products are formed because of solvent-dissolved oxygen. DISADVANTAGES 10
Development of catalysts facilitating coupling of unreactive aryl halides. Eg: Ni catalysts have been used as catalysts for coupling aryl chlorides, for the following reasons. No handling of air or moisture - sensitive material is necessary. A wide variety of functional groups are tolerated and unsymmetrical biaryls are obtained in high yields. ADVANCEMENTS 11
Xenbucin 1, an analgesic drug, was synthesized in 4 steps using two different routes. The biaryl fragment could successfully be produced via a Pd/C catalysed Suzuki coupling [5] 12 SYNTHETIC APPLICATIONS
Boscalid, a fungicide is prepared via Suzuki reaction.[6] 13
In Valsartan, the biaryls can easily be prepared by this reaction. [6] 14
The formal total synthesis of Oximidine by G.A.Molander et al. was done by using this reaction. [4] 15
The key step in the total synthesis of Myxalamide A by C.H. Heathcock et al. was Suzuki Cross-Coupling. 16
The natural anti tumour product Epothilone A was synthesized in the laboratory by J.S. Panek by using the Suzuki Cross Coupling Reaction. 17
REFERENCE 1. Jie Jack Li; Name Reactions: A Collection of Detailed Mechanisms and Synthetic Applications Fifth Edition; Springer Science & Business Media, 30-Jan-2014; Page no. 544 2. Benny K G Theng; Clay Mineral Catalysis of Organic Reactions; CRC Press, 27-Jul-2018; Page No.2016 3. Ranjit S. Dhillon; Hydroboration and Organic Synthesis : 9-Borabicclo [3.3.1] nonane (9-BBN); Springer Science & Business Media; 01 - May - 2007; Page No. 523 4. Laszlo Kurti, Barbara Czako; Strategic Applications of Named Reactions in Organic Synthesis; Elsevier, 29-Apr-2005; Page no. 37 18
4. Noora KuulojaTuula Kylm辰l辰Youjun XuRobert Franz辿n; Synthesis of Xenbucin using Suzuki reaction catalyzed by Pd/C in water; Central European Journal of Chemistry; September 2008, Volume 6, Issue 3, pp 390392 5. .A. MAUREEN ROUHI, C&EN WASHINGTON;FINE CHEMICALS Suzuki- coupling chemistry takes hold in commercial practice, from small-scale synthesis of screening compounds to industrial production of active ingredients; American Chemical Society; September 6, 2004 Volume 82, Number 36 pp. 49-58 19
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Suzuki reaction

  • 1. SUZUKI REACTION SUZUKI MIYAURA REACTION SUZUKI COUPLING REACTION SUBMITTED BY : RINSHANA FATHIMA ABDUL AZEEZ FIRST YEAR M.PHARM PHARMACEUTICAL CHEMISTRY AL SHIFA COLLEGE OF PHARMACY 1
  • 2. Suzuki reaction is the Pd catalysed cross coupling reaction[1] between the boronic / organoboronic acids / organoboranes with organic halides[2], triflates, etc under basic conditions[3] which leads to the formation of carbon carbon single bonds.[4] This reaction is commonly used for synthesising biaryl compounds. 2
  • 4. STEP 1 - Oxidative Addition - 2 groups adds to the metal. 4 MECHANISM
  • 5. STEP 2 - Hydroxide attacks Pd, kicking off X 5
  • 6. STEP 3 - Lewis base (OH鐚) attacks Lewis acid (B) 6 The Organo Boron has only 3 bonds around it and it is sp2 hybrised with an empty p orbital, making it a very good lewis acid.
  • 7. STEP 4 - Transmetallation. Carbon will attach to a metal that has an electronegativity closer to it. Electronegativity Values C = 2.5 B = 2.0 Pd = 2.4
  • 8. STEP 5 - Reductive Elimination - 2 groups are removed from a metal. 8
  • 9. ADVANTAGES Mild reaction conditions. (From 20-80) Commercial availability of many boronic acids. The inorganic by-products are easily removed from the reaction mixture, making the reaction suitable for industrial processes 9
  • 10. Generally aryl halides react sluggishly. By-products such as self-coupling products are formed because of solvent-dissolved oxygen. DISADVANTAGES 10
  • 11. Development of catalysts facilitating coupling of unreactive aryl halides. Eg: Ni catalysts have been used as catalysts for coupling aryl chlorides, for the following reasons. No handling of air or moisture - sensitive material is necessary. A wide variety of functional groups are tolerated and unsymmetrical biaryls are obtained in high yields. ADVANCEMENTS 11
  • 12. Xenbucin 1, an analgesic drug, was synthesized in 4 steps using two different routes. The biaryl fragment could successfully be produced via a Pd/C catalysed Suzuki coupling [5] 12 SYNTHETIC APPLICATIONS
  • 13. Boscalid, a fungicide is prepared via Suzuki reaction.[6] 13
  • 14. In Valsartan, the biaryls can easily be prepared by this reaction. [6] 14
  • 15. The formal total synthesis of Oximidine by G.A.Molander et al. was done by using this reaction. [4] 15
  • 16. The key step in the total synthesis of Myxalamide A by C.H. Heathcock et al. was Suzuki Cross-Coupling. 16
  • 17. The natural anti tumour product Epothilone A was synthesized in the laboratory by J.S. Panek by using the Suzuki Cross Coupling Reaction. 17
  • 18. REFERENCE 1. Jie Jack Li; Name Reactions: A Collection of Detailed Mechanisms and Synthetic Applications Fifth Edition; Springer Science & Business Media, 30-Jan-2014; Page no. 544 2. Benny K G Theng; Clay Mineral Catalysis of Organic Reactions; CRC Press, 27-Jul-2018; Page No.2016 3. Ranjit S. Dhillon; Hydroboration and Organic Synthesis : 9-Borabicclo [3.3.1] nonane (9-BBN); Springer Science & Business Media; 01 - May - 2007; Page No. 523 4. Laszlo Kurti, Barbara Czako; Strategic Applications of Named Reactions in Organic Synthesis; Elsevier, 29-Apr-2005; Page no. 37 18
  • 19. 4. Noora KuulojaTuula Kylm辰l辰Youjun XuRobert Franz辿n; Synthesis of Xenbucin using Suzuki reaction catalyzed by Pd/C in water; Central European Journal of Chemistry; September 2008, Volume 6, Issue 3, pp 390392 5. .A. MAUREEN ROUHI, C&EN WASHINGTON;FINE CHEMICALS Suzuki- coupling chemistry takes hold in commercial practice, from small-scale synthesis of screening compounds to industrial production of active ingredients; American Chemical Society; September 6, 2004 Volume 82, Number 36 pp. 49-58 19