The Concept of Multicatalysis in Aerobic Oxidation of Alcohols - Transition Metal Catalysis in Aerobic Alcohol Oxidation - page 188

Table 7.4 Multicatalytic oxidation-olefination reaction.

i -Pr i -Pr

1. 39 (2.5 mol % )
Bu 4 NOAc (5 mol %)
tolue ne, MS 3 Å, O 2 (1 atm)

OH O

NN

R 1 R 2 R 1 R 2

2. RhCl( PPh 3 ) 3 40 (5 mol % )
i -Pr OH, TMSCHN 2 ,PPh 3
1,4-d ioxa ne, 50 °C

Pd

i -Pr i -Pr

AcO

OA c

O

H H

39

Entry Substrate Product Yield (%)

1 78

TBSO OH TBSO

41 42

OH

2 82

43 44

Me O MeO

O O

3 92 OH

45 46

O O

OH

4 84

Bn O

BnO

47 48

OBn

OBn

5 65

OH

49 50

OH

6 87

Bn O

BnO

52

51

OH

7 54

Bn O

BnO

OH

53 54

1. 39 (2.5 mol %), Bu 4 NOAc (5 mol %)
toluene, MS 3Å, O 2 (1 atm), 60 °C, 12 h
2. 40 (2.5 mol %), i -PrOH, TMSCHN 2 ,
PPh 3 , 1,4-dioxane, 50 °C

OBn

OH

OBn

3. AlCl 3 , 50 °C, 2 h
4. 55 (10 mol %), 1,4-dioxane, 50 °C

51

56 , 70%

(7.10)

N N

Cl

Ru

Cl

Ph

55

PCy 3