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. Author manuscript; available in PMC: 2022 Aug 3.
Published in final edited form as: Bioorg Chem. 2020 Jun 15;101:104017. doi: 10.1016/j.bioorg.2020.104017

Table 1.

Reaction yields (in parentheses) using system Aa or Bb

graphic file with name nihms-1604321-t0005.jpg
Yield (%)
Entry Thiol (R) System A (r.t.) System B (r.t.) System B (heat)
Diaryl disulfide Diaryl thiosulfonate Diaryl disulfide Diaryl thiosulfonate Diaryl disulfide Diaryl thiosulfonate
1 1a (o-F) 2a (74.3) 3a (10.2) 2a (72.0) 3a (12.4) 2a (6.2) 3a (87.0)
2 1b (m-F) 2b (54.0) - 2b (61.5) 3bc (20.3) 2b (16.5) 3bc (63.0)
3 1c (p-F) 2c (83.0) 3c (13.7) 2c (78.3) 3c (9.0) 2c (0.0) 3c (95.0)
4 1d (o-Cl) 2d (63.2) 3d (15.5) 2d (69.9) 3d (11.5) 2d (0.0) 3d (83.8)
5 1e (m-Cl) - - - - 2e (18.5) 3e (67.3)
6 1f (p-Cl) 2f (70.2) 3f (12.0) 2f (75.0) 3f (13.8) 2f (0.0) 3f (92.0)
7 1g (o-Br) 2g (47.6) 3g (9.2) 2g (35.8) 3g (0.0) 2g (9.3) 3gc (80.6)
8 1h (m-Br) 2h (59.3) 3h (0.0) 2h (44.1) 3h (0.0) 2h (10.1) 3h (84.4)
9 1i (p-Br) 2i (76.6) 3i (0.0) 2i (62.7) 3i (17.0) 2i (0.0) 3i (93.0)
a

AgNO3/BF3·OEt2, ACN (dry)

b

Al(H2PO4)3-HNO3, ACN (dry)

(−)

reaction not performed