Table 1 Optimization conditions for the aza-Diels–Alder reaction.

From: Cerium(III) immobilized on the functionalized halloysite as a highly efficient catalyst for aza-Diels–Alder reaction

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Entry

Catalyst, amount (g)

Solvent

Temp. (°C)

Time (h)

Yield (%)

1

Ce/Hal-TCT-IDA, 0.05

CH2Cl2

25

1

–

2

Ce/Hal-TCT-IDA, 0.05

CH2Cl2

25

5

54

3

Ce/Hal-TCT-IDA, 0.05

CH2Cl2

25

12

91

4

Ce/Hal-TCT-IDA, 0.05

CH2Cl2

30

12

86

5

Ce/Hal-TCT-IDA, 0.05

CH2Cl2

Reflux

12

80

6

–

CH2Cl2

25

12

20

7

Ce/Hal-TCT-IDA, 0.01

CH2Cl2

25

12

70

8

Ce/Hal-TCT-IDA, 0.03

CH2Cl2

25

12

79

9

Ce/Hal-TCT-IDA, 0.07

CH2Cl2

25

12

92

10

Ce/Hal-TCT-IDA, 0.05

MeCN

25

12

21

11

Ce/Hal-TCT-IDA, 0.05

EtOH

25

12

61

12

Ce/Hal-TCT-IDA, 0.05

Toluene

25

12

40

13

Ce(NO3)3, 0.01

CH2Cl2

25

12

82

  1. Imine 1 (1 mmol), styrene (1.5 mmol).
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