Table 1 Optimization studiesa
From: Organomediated electrochemical fluorosulfonylation of aryl triflates via selective C–O bond cleavage
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|---|---|---|
Entry | Alteration | Yield of 3a (3b) (%)b |
1 | None | 75 (0) |
2 | M-2 instead of M-1 | 41 (35) |
3 | M-3 instead of M-1 | 49 (31) |
4 | M-4 instead of M-1 | 0 (82) |
5 | M-5 instead of M-1 | 0 (82) |
6 | M-6 instead of M-1 | 0 (88) |
7 | without M-1 | 0 (83) |
8 | 25 mol% instead of 20 mol% M-1 | 74 (0) |
9 | 15 mol% instead of 20 mol% M-1 | 67(0) |
10 | nBu4NPF6, Et4NOTs, LiClO4 instead of nBu4NClO4 | 70 (0)/52 (0)/ 61 (0) |
11 | C(+)|C(−), Pt(+)|C(−), C(+)|Pt(−), RVC(+)|RVC(−), RVC(+)|Pt(−) instead of Pt(+)|RVC(−) | 32 (42)/ 21 (63)/65 (16)/16 (53)/57 (20) |
12 | TBAF·H2O, NaPF6, KF instead of KHF2 | 9 (0)/23 (0)/trace (0) |
13 | 10 mA or 15 mA instead of 12 mA | 37 (0)/ 56 (8) |
14 | No electric current | No reaction |
15 | ArOMe, ArOAc, ArOPO(OMe)2, ArBr or ArI instead of 1a | 0/0/0/0/0 |
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