Table 1 Screening of reaction conditions for cross-coupling of IQMA 1a and 2-naphthol 2aa.

From: Bayesian optimization-driven parallel-screening of multiple parameters for the flow synthesis of biaryl compounds

View full size image

Entry

micro mixer

2a (equiv.)

TfOH (mol%)

Temp. (˚C)

Conc. of 1a (M)

Flow rate (mL/min)

Residence time (min)

NMR yieldb (%)

1

Comet Xc

2.0

1.0

60

0.05

0.05

24

68

2

Comet X

3.0

0.5

40

0.01

0.2

6

73

3

β-typed

1.0

2.0

60

0.01

0.1

13.5

42

4

β-type

3.0

0.5

20

0.1

0.1

13.5

28

5

T-shapede

1.0

2.0

40

0.05

0.05

16

55

6

T-shaped

2.0

1.0

20

0.1

0.2

4

75

7

T-shaped

2.0

1.0

20

0.1

0.15

5.5

81

8

Comet X

2.3

1.0

55

0.039

0.04

30

77

9

β-type

1.1

2.4

85

0.15

0.1

13.5

40

10

T-shaped

1.3

1.2

15

0.11

0.15

5.5

78

11

T-shaped

2.1

1.1

30

0.061

0.15

5.5

76

12

Comet X

2.8

1.0

50

0.014

0.11

11

79

13

Comet X

3.4

1.3

55

0.01

0.032

37.5

88

14

Comet X

2.2

1.7

15

0.1

0.014

85.5

44

15

Comet X

3.0

1.5

25

0.015

0.08

15

96 (93)f

  1. aReaction conditions: 1a (0.065 mmol), 2a, and TfOH, in degassed dry toluene.
  2. b1,3,5-Trimethoxybenzene was used as a standard.
  3. cVolume of Comet X microreactor = 2.4 mL.
  4. dVolume of β-type microreactor = 2.7 mL.
  5. eVolume of T-shaped microreactor = 1.6 mL.
  6. fIsolated yield.
Back to article page