buchwald hartwig coupling.ppt

advanced organic reactions

1. Buchwald-Hartwig Coupling
&
Click reaction
U-5 New synthetic Organic Reactions
B.SATEESH KUMAR
L.IN CHEMISTRY,GDCM SKLM
III BSc Chemistry
Semester-VI
Paper-VIII C-2
Part-8

2. Outlines
•U-5 Total syllabus
•Short notes on coupling reactions
•About the Buchwald -hartwigCoupling Reaction
Statement with equation
Mechanism
•About Click Reaction
Statement with equation
Mechanism
•Conclusions
B SATEESH KUMAR , L IN CHEMISTRY , GDC M SKLM

3. Unit-5
[New synthetic reactions]
1.Baylis-Hillmann reaction
2.Grubbs catalysts
3.Grubbs RCM olefin metathesisreaction
4.Mukayama aldol reaction
5.Mcmurry reaction
6.Mitsnobu reaction
7.Julia-lythgoeolefination
8.Peterson olefination
9. Heck reaction
10. Suzuki coupling
11. Stille coupling
12. Sonogishira coupling
13. Buchwald -hartwig coupling
14. Click reaction
15. Ugireaction
B SATEESH KUMAR , L IN CHEMISTRY , GDC M SKLM

4. Buchwald -HartwigCoupling
Reaction
B SATEESH KUMAR , L IN CHEMISTRY , GDC M SKLM
Start
with

5. About the reaction
•It is a one of the amination reaction inorganic chemistry
•In this reaction a new C-N bond formation reaction
•ThisBuchwald–Hartwigamination reaction is apalladium-catalyzed
cross coupling reaction.
•Here new C-N bond formed between of amines witharyl halides
•In this coupling reaction requirement of Base is important.
B SATEESH KUMAR , L IN CHEMISTRY , GDC M SKLM

6. Statement
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“Couplingofarylhalideandaprimaryorsecondaryamineinthe
presenceofbaseandpalladium(0)catalysttoformarylamine.
This coupling reaction is known as a Buchwald -hartwig Coupling
reaction”.

7. Aryl halide
Reaction
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AMINE Aryl amines

8. It is a Catalytic cycle mechanism I
Consists of 3 main steps
namely
1.Oxidative Addition
2.Substitution of amine
3.Reductive elimination
Mechanism
B SATEESH KUMAR , L IN CHEMISTRY , GDC M SKLM

9. TOTAL MECHANISM
OXIDATIVE ADDITION
SUBSTITUTION
REDUCTIVE
ELIMINATION
1
2
3
B SATEESH KUMAR , L IN CHEMISTRY , GDC M SKLM

10. Click reaction 2
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11. 1.The classicclick reactionis the copper-catalyzedreactionof an azide
with an alkyneto form a 5-membered heteroatom ring this reaction is
known as a Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC).
2.The first triazole synthesis, from diethyl acetylenedicarboxylate and
phenyl azide, was reported by Arthur Michael in 1893.
CLICK REACTION
B SATEESH KUMAR , L IN CHEMISTRY , GDC M SKLM

12. The1,3-dipolar cycloadditionis achemical reaction between
a1,3-dipole and adipolarophileto form a five-membered ring.
1,3-dipolar cycloaddition
B SATEESH KUMAR , L IN CHEMISTRY , GDC M SKLM

13. Reaction
1,3 dipolar addition Organo azide with alkyne in the presence o heat to
form 1,2,3 triazole
1,2,3 triazole

14. Clear cut reaction

15. 1.Have a simple reaction conditions
2.Use readily available starting materials and reagents
3.Use no solvent or use a solvent that is benign or easily
removed (preferably water)
4.Provide simple product isolation by non-
chromatographic methods (crystallisation ordistillation)
5.Have highatom economy.
The process would
preferably

16. Thank You
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