Table 1 Optimization of reaction conditions

From: [3+2] Cycloaddition of alkyl aldehydes and alkynes enabled by photoinduced hydrogen atom transfer

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Entry

Deviations from abovea

Yield (%)b

1

none

88

2

NaDT instead of TBADT

83

3

MeCN instead of MeCN/H2O

75

4

DMSO instead of MeCN/H2O

trace

5

acetone instead of MeCN/H2O

65

6

DMF instead of MeCN/H2O

43

7

without TBADT

0

8

without LED irradiation

0

  1. TBADT tetra-n-butylammonium decatungstate, NaDT sodium decatungstate, MeCN acetonitrile, DMSO dimethylsulfoxide, DMF N,N-dimethylformamide.
  2. aReaction conditions: 1a (0.4 mmol), 2a (0.2 mmol), TBADT (2 mol%), MeCN/H2O (10:1), purple LEDs, 390 nm, 25 °C, 10 h.
  3. bIsolated yield.
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