Table 1 Optimization of Reaction Conditionsa

From: Copper-catalyzed Z-selective synthesis of acrylamides and polyacrylamides via alkylidene ketenimines

View full size image

Entry

Catalyst

Loading [mol%]

Base

Solvent

Yield [%]b

1

Cu(MeCN)4BF4

10

DIPEA

CHCl3

62

2

CuOTf

10

DIPEA

CHCl3

24

3

CuI

10

DIPEA

CHCl3

75

4

CuBr

10

DIPEA

CHCl3

81

5

CuBr

5

DIPEA

CHCl3

56

6

CuBr

20

DIPEA

CHCl3

79

7

CuBr

10

–

CHCl3

n.r.

8

CuBr

10

TEA

CHCl3

65

9

CuBr

10

DMAP

CHCl3

trace

10

CuBr

10

DBU

CHCl3

trace

11

CuBr

10

K2CO3

CHCl3

20

12

CuBr

10

DIPEA

DCM

75

13

CuBr

10

DIPEA

toluene

61

14

CuBr

10

DIPEA

THF

45

15

CuBr

10

DIPEA

DMF

48

16

CuBr

10

DIPEA

H2O

trace

17c

CuBr

10

DIPEA

CHCl3

n.r.

18d

CuBr

10

DIPEA

CHCl3

n.r.

  1. aConditions: 1a (1.0 equiv), 2a (1.5 equiv), H2O (1.0 equiv), base (2.0 equiv), HPO(OMe)2 (0.1 equiv), solvent (0.1 M), room temperature for 6 h.
  2. bDetermined by 1H NMR of the crude mixture with an internal standard.
  3. cWithout HPO(OMe)2.
  4. dThe reaction was set up without addition of water in absolutely anhydrous CHCl3 with 4 Å MS.
Back to article page