Table 1 Optimization of the reaction conditionsa

From: Visible-light-promoted direct desulfurization of glycosyl thiols to access C-glycosides

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Entry

Deviation from standard conditions

Yieldb (%)

1

none

85

2

DMSO instead of MeCN

81

3

DCM instead of MeCN

78

4

THF instead of MeCN

63

5

Cs2CO3 instead of Et3N

80

6

DABCO instead of Et3N

43

7

DBU instead of Et3N

38

8

No Et3N

nd

9

No HE

nd

10

Air atmosphere

<5

11

Without visible light irradiation

nd

  1. HE Hantzsch ester.
  2. aUnless otherwise noted, reactions were performed with mixtures of 8 (0.05 mmol), 9 (2.0 equiv.), MeCN (0.1 M), at rt under irradiation by blue LED for 8 h.
  3. bYields were determined by 1H NMR spectroscopy using 1,3,5-trimethoxybenzene as an internal standard.