Table 4. Photo-induced C–C bond formation of alkyl bromide.
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Entry | Cat. | Reaction time (h) | Substrate | Product | Conv.; yield f (%) |
1 a , c | Pd-N-1 | 10 | 90; 83 | ||
2 a , d | Pd-B-1 | 10 | 0; 0 | ||
3 d , e | Pd-B-1 | 10 | 30; 15 | ||
4 b , c | Pd-N-1 | 10 | 84; 63 | ||
5 b , c | Pd-N-1 | 10 | 88; 66 | ||
6 a , c | Pd-N-1 | 20 | 90; 68 |
aProcedure a: Pd(ii) complex (1 mol%) iPr2NEt (2 equiv.), CH3CN.
bProcedure b: Pd(ii) complex (1 mol%) iPr2NEt (5 equiv.), HCO2H (2 equiv.), CH3CN.
cThe reaction mixture was irradiated with a blue LED (λmax = 462 nm)
dThe reaction mixture was irradiated with a xenon lamp (λex > 370 nm).
eThe procedure is the same as a except TMEDA was used instead of iPr2NEt.
fDetermined by 1H NMR spectroscopy using 4,4′-dimethyl-2,2′-bipyridine as an internal standard. Ts = Tosylate.