grignard reaction key features: handling of air/ moisture sensitive chemicals, formation of c-c...

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Grignard Reaction CH 3 O R M gX OH R CH 3 Key features: Handling of air/ moisture sensitive chemicals, formation of C-C bond. n-Butyl lithium Key features: Strong base such as KO t Bu, NaH, n-BuLi handled. Boron trifluoride etherate Key features: Moisture sensitive catalyst BF 3 :Et 2 O handled . OH RX O R n-B uLi O O R N aB H 4 BF 3 Et 2 O OH Reaction Handled

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Page 1: Grignard Reaction Key features: Handling of air/ moisture sensitive chemicals, formation of C-C bond. n-Butyl lithium Key features: Strong base such as

Grignard Reaction CH3

O

RMgX

OH

R

CH3

Key features: Handling of air/ moisture sensitive chemicals, formation of C-C bond.

n-Butyl lithium

Key features: Strong base such as KOtBu, NaH, n-BuLi handled.

Boron trifluoride etherate

Key features: Moisture sensitive catalyst BF3:Et2O handled .

OH

RX

ORn-BuLi

O

OR NaBH4

BF3 Et2O

OH

Reaction Handled

Page 2: Grignard Reaction Key features: Handling of air/ moisture sensitive chemicals, formation of C-C bond. n-Butyl lithium Key features: Strong base such as

B(OH)2 X Pd catalyst

Key features: Handling of air/ moisture sensitive chemicals, formation of C-C bond.

Suzuki Coupling

Key features: Handling of air sensitive reagents, Aromatic C-C bond formation.

Negishi Coupling ZnX X Pd catalyst

Gomberg Reaction

Key features: Handling of diazonium salt. Aromatic C-C bond formation.

N2 X H OH

Reaction Handled

Page 3: Grignard Reaction Key features: Handling of air/ moisture sensitive chemicals, formation of C-C bond. n-Butyl lithium Key features: Strong base such as

Ritter Reaction

OH CO2OH

COOH

Key features: Displacement of tertiary alcohol group with amido group.

Vilsmeier-Haack Reaction

Key features: POCl3 handling. Typical formylation reaction.

Kolbe Carboxylation

Key features: Handling of high pressure reaction.

Ph

PhOH RCN

Acid

Ph NH

R

Ph O

N

POCl3

DMFN

H

O

R

R'

R

R'

Reaction Handled

Page 4: Grignard Reaction Key features: Handling of air/ moisture sensitive chemicals, formation of C-C bond. n-Butyl lithium Key features: Strong base such as

Birch Reduction Na, NH3

Key features: Handling of pyrophoric metals. Aromatic reduction.

Baeyer-Villiger Oxidation

Key features: Handling of reactive chemical, like peracid, Peroxide, etc.

Borane Reduction

OR

O

BH3 Me2S OH

Key features: Pyrophoric BDMS handled.

R

O

CH3COOOH O R

O

Reaction Handled

Page 5: Grignard Reaction Key features: Handling of air/ moisture sensitive chemicals, formation of C-C bond. n-Butyl lithium Key features: Strong base such as

NH2

O

NaOBr NH2Hofmann Rearrangement

Key features: Hypobromite handled. Synthesis of amine from ketone.

Reformatsky Reaction

Key features: Handling of sensitive organometallic reagent

Skraup Synthesis

Key features: Oxidation using H2SO4 and Nitrobenzene.

O

BrOEt

OZn

OEtHO

O

NH2

HO OH

OH H2SO4

PhNO2

N

Reaction Handled

Page 6: Grignard Reaction Key features: Handling of air/ moisture sensitive chemicals, formation of C-C bond. n-Butyl lithium Key features: Strong base such as

Chiral Separation

CH3

O

Chiral catalyst CH3

OH

CH3

O

Chiral metal catalyst

H2

CH3

OH

Key features: Separation of racemic pure compound.

Asymmetric Hydrogenation

Key features: Synthesis of optically pure compound.

Asymmetric Reduction

Key features: Handeled pyrophoric reagents. High ee achieved.

H3C

NHEt

L-Tartaric Acid

H3C

NHEt

Reaction Handled

Page 7: Grignard Reaction Key features: Handling of air/ moisture sensitive chemicals, formation of C-C bond. n-Butyl lithium Key features: Strong base such as

Transesterification

S X S SO2NH2

n-BuLi, SO2 gas

NH3

O

NNN

O NN

N

Key features: Acid/ base catalyzed transesterification.

Click Chemistry

Key features: One-pot triazole chemistry.

Thiophene Chemistry

Key features: Handeled n-BuLi, sulfur dioxide gas.

R''O R

O

R'OH R'O R

O

R''OH

Reaction Handled