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. 2016 Jun 15;7(9):6083–6098. doi: 10.1039/c6sc00462h

Table 4. Photo-induced C–C bond formation of alkyl bromide.

Inline graphic
Entry Cat. Reaction time (h) Substrate Product Conv.; yield f (%)
1 a , c Pd-N-1 10 graphic file with name c6sc00462h-u2.jpg graphic file with name c6sc00462h-u3.jpg 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 graphic file with name c6sc00462h-u4.jpg graphic file with name c6sc00462h-u5.jpg 84; 63
5 b , c Pd-N-1 10 graphic file with name c6sc00462h-u6.jpg graphic file with name c6sc00462h-u7.jpg 88; 66
6 a , c Pd-N-1 20 graphic file with name c6sc00462h-u8.jpg graphic file with name c6sc00462h-u9.jpg 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.