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. 2010 Aug 18;6:880–921. doi: 10.3762/bjoc.6.88

Table 6.

Reactions of thiophenoxides with CF3Br under UV irradiation and pressure of reaction gas [179].

graphic file with name Beilstein_J_Org_Chem-06-880-i004.jpg

R Solvent Base p (atm) T (°C) Irradiation time, (h) Conversion of ArSH, (%) Isolated yields of ArSCF3 (%)

4-CH3 DMF Et3N 4–5 10–13 1.5 82
4-NH2 DMF Et3N 4.5–6 10–20 2 76.4
3-NH2 HMPA morpholine 3–4 17–19 3.25 63.5a
4-NHCOMe DMF Et3N 3.5 19 2.7 69
4-NHCO2Me DMF Et3N 4.5–5 15–25 1.2 63 55.5
HMPA morpholine 2–5 8–10 2.5 73 83.6
4-Cl CH3CN Et3N 3–3.5 15–18 2.8 53 43a
DMF Et3N 3–3.5 14 1.2 100 48a
HMPA Et3N 4 8–10 1 100 69
HMPA morpholine 3–4 14–16 3.5 97 62.5
HMPA morpholine 3–4.5 29–30 3 36 46
Sulfolane morpholine 3.5 23 2 19.5 5.4
N-Methyl pyrrolidone morpholine 3.5 17 2.2 35.5 14.3

aDetermined by GLC.