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. 2016 Jul 12;7(10):6407–6412. doi: 10.1039/c6sc02653b

Table 1. Minisci C–H alkylation of 1 under visible light.

Inline graphic
Entry Reagents (equiv.) Solvents t (°C)/time (h) Yield a (%) 3a
1 2a (1.5), AgNO3 (0.2), K2S2O8 (3) DCM/H2O 30/24 18
2 2b (1.5), Mn(OAc)3 (2.5), TFA (1) AcOH/H2O 50/18 30
3 2a (1.5), Bl-OAc (2), Ru(bpy)3Cl2 (0.01), VL b DCM 30/24 33
4 2a (1.5), Bl-OAc (2), Ru(bpy)3Cl2 (0.01), VL CH3CN 30/24 38
5 2a (1.5), Bl-OAc (2), Ru(bpy)3Cl2 (0.01), VL, Ar HFIP 30/24 88 (82 c )
6 2b (1.5), Bl-OAc (2), Ru(bpy)3Cl2 (0.01), VL HFIP 30/24 59
7 2a (1.5), Bl-OH (2), Ru(bpy)3Cl2 (0.01), VL HFIP 30/24 82
8 2a (1.5), Bl-OMe (2), Ru(bpy)3Cl2 (0.01), VL HFIP 30/24 61
9 2a (1.5), Bl-N3 (2), Ru(bpy)3Cl2 (0.01), VL HFIP 30/24 25
10 2a (1.5), Bl-Cl (2), Ru(bpy)3Cl2 (0.01), VL HFIP 30/24 <2
11 2a (1.5), PhI(OAc)2 (2), Ru(bpy)3Cl2 (0.01), VL HFIP 30/24 <2
12 2a (1.5), Bl-OAc (2), Ir(ppy)3 (0.01), VL HFIP 30/24 22
13 2a (1.5), Bl-OAc (2), VL HFIP 30/24 <2
14 2a (1.5), Bl-OAc (2), Ru(bpy)3Cl2 (0.01), in darkness HFIP 30/24 <2
15 2a (1.5), Bl-OAc (2), TEMPO (2), Ru(bpy)3Cl2 (0.01), VL HFIP 30/24 <2

aYields are based on 1H-NMR analysis on a 0.2 mmol scale.

bVL: compact household fluorescent bulb, 20 W.

cIsolated yield.