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. 2023 Aug 8;13(33):23359–23364. doi: 10.1039/d3ra04512a

Optimization of the reaction conditionsa.

graphic file with name d3ra04512a-u1.jpg
Entry Equiv. 2a Solvent Additive Light Yieldb (%)
1 10 DMA None 390 nm 65
2 10 DMA K2CO3 390 nm 82 (75)c
3 10 DMA DABCO 390 nm 80
4 10 Acetone K2CO3 390 nm 81
5 10 MeCN K2CO3 390 nm 88
6 10 DCM K2CO3 390 nm 85
7 10 MeCN K2CO3 390 nm 87
8 10 MeCN K3PO4 390 nm 84
9 10 MeCN KHCO3 390 nm 90
10 10 MeCN KHCO3 Dark <10
11 5 MeCN KHCO3 390 nm 89
12 2.5 MeCN KHCO3 390 nm 75
13 5 MeCN KHCO 3 390 nm 87 d
14 5 MeCN KHCO3 456 nm 88
15 5 Wet MeCN KHCO3 390 nm 53d
a

Reaction conditions: 0.1 mmol of TT salt 1a, 0.1 mmol of the corresponding additive, indicated amounts of phosphite 2a and 0.1 M in the indicated dry solvent.

b

Determined by 1H NMR using 1,3,5-trimethoxybenzene as internal standard.

c

Isolated yield from 0.5 mmol of 1a.

d

30 minutes reaction time.