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. 2022 Dec 19;145(1):345–358. doi: 10.1021/jacs.2c10090

Table 1. Reactivity of Cyclic Diaryl Hypervalent λ3-Reagents.

graphic file with name ja2c10090_0015.jpg

      yieldsb
entry X(III)-OTf conditionsa C–C C–O
1 4a-OTf Cs2CO3; CHCI3 no conversion
2 3a-OTf 15% 70%
3 2a-OTf 35% 35%
4 4a-OTf K2CO3; CHCI3 no conversion
5 3a-OTf 26% 9%
6 2a-OTf 49% traces
7 4a-OTf K2CO3; H2O no conversion
8 3a-OTf no conversion
9 2a-OTf 13% 60%
a

Conditions: 0.1 mmol of X(III)-OTf reagent (4a-OTf, 3a-Tf, 2a-OTf), 0.15 mmol of 5a, and 0.3 mmol of Cs2CO3 or K2CO3 in 1 mL of CHCl3 or H2O at room temperature for 16h.

b

Isolated yields.