Table 1 Optimization of copper-catalyzed photoredox Chan-Lam coupling of 1a with 2a.

From: Autocatalytic photoredox Chan-Lam coupling of free diaryl sulfoximines with arylboronic acids

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Entry

catalyst/mol %

Solvent

Conc./M

Assay yielda/%

1

Cu(OAc)2.H2O/20

MeOH

0.3

25

2

CuCl/20

MeOH

0.3

5

3

CuF2/20

MeOH

0.3

30

4

Cu(O2CCF3)2.H2O/20

MeOH

0.3

36

5

Cu(O2CCF3)2.H2O/20

EtOH

0.3

90

6

Cu(O2CCF3)2.H2O/20

iPrOH

0.3

49

7

Cu(O2CCF3)2.H2O/20

tBuOH

0.3

0

8

Cu(O2CCF3)2.H2O/10

EtOH

0.3

90

9

Cu(O2CCF3)2.H2O/5

EtOH

0.3

45

10b

Cu(O2CCF3)2.H2O/10

EtOH

0.3

90

11c

Cu(O2CCF3)2.H2O/10

EtOH

0.3

75

12b

Cu(O2CCF3)2.H2O/10

EtOH

1.5

95(94d)

13b

Cu(O2CCF3)2.H2O/10

EtOH

2.0

85

14b

-

EtOH

1.5

0

15e

Cu(O2CCF3)2.H2O/10

EtOH

1.5

17(20f)

16 g

Cu(O2CCF3)2.H2O/10

EtOH

1.5

66

  1. General conditions: unless otherwise stated, reactions were carried out with 1a (0.3 mmol) and 2a (2.3 equiv) at room temperature under argon for 48 h.
  2. aAssay yields determined by 1H NMR using 0.1 mmol CH2Br2 (7.0 μL) as internal standard.
  3. b2a (2.0 equiv).
  4. c2a (1.5 equiv).
  5. dIsolated yield.
  6. ePhenyl boronic acid pinacol ester employed.
  7. fB(OH)3 (3.0 equiv) as an additive.
  8. gPotassium phenyl trifluoroborate (3.0 equiv) employed for 72 h.
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