Table 1.
Examination of different types of Cu complexes.[a]
| ||||
|---|---|---|---|---|
| Entry | Ligand; Mol % | Conv. [%];[b] Yield [%][c] |
SN2′:SN2 (3a:4a)[b] | e.r.[d] |
| 1 | none[a] | 45; 21 | <2:>98 | NA |
| 2 | 5; 11 | 80; 76 | 2:98 | NA |
| 3 | 6; 11 | 65; 41 | 7:93 | ND |
| 4 | 7; 11 | >98; 73 | 5:95 | ND |
| 5 | 8; 11 | >98; 54 | 20:80 | ND |
| 6 | 9; 11 | >98; 69 | <2:>98 | NA |
| 7 | 10; 11 | >98; 77 | 76:24 | 97:3 |
| 8 | 11a; 5.5 | >98; 83 | 95:5 | 97:3 |
| Entry | Ligand; Mol % | Conv. [%];[b] Yield [%][c] |
SN2′:SN2 (3a:4a)[b] | e.r.[d] |
|---|---|---|---|---|
| 1 | None[a] | 45; 21 | <2:>98 | NA |
| 2 | 5; 11 | 80; 76 | 2:98 | NA |
| 3 | 6; 11 | 65; 41 | 7:93 | ND |
| 4 | 7; 11 | >98; 73 | 5:95 | ND |
| 5 | 8; 11 | >98; 54 | 20:80 | ND |
| 6 | 9; 11 | >98; 69 | <2:>98 | NA |
| 7 | 10; 11 | >98; 77 | 76:24 | 97:3 |
| 8 | 11; 5.5 | >98; 83 | 95:5 | 97:3 |
[a]
Performed under N2 atm; ≤5% linear methoxy addition products are observed in all cases.
[b]
Conv. and SN2′:SN2 ratios determined by analysis of 1H NMR spectra of unpurified mixtures; conv. (±2%) refers to disappearance of the 2a.
[c]
Yields of isolated and purified products but as a mixture of 3a and 4a (±5%).
[d]
E.r. values determined by HPLC (±1%). See the Supporting Information for details.
Abbreviations: Mes, 2,4,6-(Me)3-C6H2; NA, not applicable ND; not determined.