The Suzuki reaction is an organic reaction, classified as a cross-coupling reaction, where the coupling partners are a boronic acid and an organohalide catalyzed by a palladium(0) complex. It was first published in 1979 by Akira Suzuki and he shared the 2010 Nobel Prize in Chemistry with Richard F.

1. 1
Mechanism & Synthetic
Application of SUZUKI
REACTION
Presented by
Rudraprasad Sahoo
M. Pharm 1st semester
Department of Pharmaceutical Chemistry
Institute of Pharmacy & Technology,
Salipur.

2. Contents
Stats about Akira Suzuki
Reagents and solvent systems
About the chemical reaction
Mechanism of Suzuki reaction
Some synthetic uses of Suzuki reaction
References
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3. Some stats about Akira Suzuki
 Born September 12, 1930
 Place-Mukawa, Hokkaidō,Japan
 Nationality - Japanease
 Alma mater Hokkaidō University
 Known for Suzuki reaction
 Awards Nobel Prize for Chemistry
(2010)
 Person of Cultural Merit (2010)
 Order of Culture (2010)
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4. The reagents and solvents
Reagents
Palladium metal
Sodium tert. Butoxide
Organoborane
compounds
Sodium Carbonate
Solvents
Benzene
Toluene
Tetrahydro Furan
Dimethyl
Formamide
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5. What is Suzuki reaction
The Suzuki reaction is an organic reaction,
classified as a cross-coupling reaction,
where the coupling partners are a boronic
acid and an organohalide catalyzed by a
palladium complex.
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6. Mechanism of Suzuki reaction
1. The first step is the oxidative addition of palladium to the halide to
form the organo-palladium species.
2. Reaction with base gives intermediates which via transmetalation with
the boronate complex, forms the organo-palladium species.
3. Boronate complex is produced by reaction of boronic acid with base.
4. Reductive elimination of the desired product restores original
palladium catalyst that completes the reaction cycle.
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7. Mechanism of Suzuki reaction
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8. Oxidative Addition
 In most cases the oxidative addition is the rate
determining step of the catalytic cycle.
 During this step, the palladium catalyst is oxidized from
palladium(0) to palladium(II). The palladium catalyst 1 is
coupled with the alkyl halide 2 to yield an
organopalladium complex
 As seen in the diagram below, the oxidative addition step
breaks the carbon-halogen bond where the palladium is
now bound to both the halogen and the R group.
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9. Continued
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10. Transmetalation
 Transmetalation is an organometallic reaction where ligands are
transferred from one species to another.
 In the case of the Suzuki coupling the ligands are transferred
from the organoboron species 6 to the palladium(II) complex 4
where the base that was added in the prior step is exchanged
with the R1 substituent on the organoboron species to give the
new palladium(II) complex 8.
 The organoboron compounds do not undergo transmetalation in
the absence of base and it is therefore widely believed that the
role of the base is to activate the organoboron compound as well
as facilitate the formation of R2-Pdll-OtBu from R2-Pdll-X.
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11. Continued
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12. Reductive Elimination
 The final step is the reductive elimination step where the
palladium(II) complex (8) eliminates the product (9) and
regenerates the palladium(0) catalyst(1).
 Ridgway et al. have shown the reductive elimination
proceeds with retention of stereochemistry.
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13. Continued
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14. Synthetic application of Suzuki reaction
 Besides a wide range of industrial uses, The
synthetic application of Suzuki reaction is the
synthesis of some complex natural compounds
like caparratriene, a derivative of citronellel,
an anti leukemic drug.
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15. Industrial uses of the Suzuki reaction
Another example is the coupling of 3-
pyridylborane and 1-bromo-3-
(methylsulfonyl)benzene that formed an
intermediate that was used in the
synthesis of a potential central nervous
system agent.
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3-pyridylborane1-bromo-3-
(methylsulfonyl)benzene

16. Reference
1. Miyaura, Norio; Yamada, Kinji; Suzuki, Akira (1979). "A new stereospecific cross-coupling by
the palladium-catalyzed reaction of 1-alkenylboranes with 1-alkenyl or 1-alkynyl
halides". Tetrahedron Letters. 20 (36): 3437–3440. doi:10.1016/S0040-4039(01)95429-
2. hdl:2115/44006.
2. Miyaura, Norio; Suzuki, Akira (1979). "Stereoselective synthesis of arylated (E)-alkenes by
the reaction of alk-1-enylboranes with aryl halides in the presence of palladium
catalyst". Chem. Comm. 0 (19): 866–867. doi:10.1039/C39790000866.
3. 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.
4. Nobelprize.org. "The Nobel Prize in Chemistry 2010". Nobel Prize Foundation.
Retrieved 2013-10-25.
5. Suzuki, Akira (1991). "Synthetic Studies via the cross-coupling reaction of organoboron
derivatives with organic halides". Pure Appl. Chem. 63 (3): 419–
422. doi:10.1351/pac199163030419.
6. Miyaura, Norio; Suzuki, Akira (1979). "Palladium-Catalyzed Cross-Coupling Reactions of
Organoboron Compounds". Chemical Reviews. 95 (7): 2457–
2483. CiteSeerX 10.1.1.735.7660. doi:10.1021/cr00039a007.(Review)
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