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. 2014 Mar 7;10:622–627. doi: 10.3762/bjoc.10.53

Table 2.

Scope of the photocatalytic bromination of phenols.

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Entry Substrate Product Yield (%)a
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1 R1 = TMS; R2 = OMe; R3 = H 88
2 R1 = TMS; R2 = Me; R3 = H 69
3 R1 = TMS; R2 = Cl; R3 = H 58
4 R1 = TBS; R2 = OMe; R3 = H 85
5 R1 = MOM; R2 = Me; R3 = H 97
graphic file with name Beilstein_J_Org_Chem-10-622-i005.jpg graphic file with name Beilstein_J_Org_Chem-10-622-i006.jpg
6 R1 = TMS; R3 = H (3:2)c 79
7 R1 = THP; R3 = H (3:2)c 79
graphic file with name Beilstein_J_Org_Chem-10-622-i007.jpg graphic file with name Beilstein_J_Org_Chem-10-622-i008.jpg
8 R1 = TMS; R2 = OMe; R3 = H (2:1)c 73
9 R1 = Ms; R2 = OMe; R3 = Ms (5:1)c 95
10 R1 = Bn; R2 = OMe; R3 = Bn (5:3)c 98
11 R1 = H; R2 = OMe; R3 = H (3:2)c 40
12 graphic file with name Beilstein_J_Org_Chem-10-622-i009.jpg graphic file with name Beilstein_J_Org_Chem-10-622-i010.jpg 84
graphic file with name Beilstein_J_Org_Chem-10-622-i011.jpg graphic file with name Beilstein_J_Org_Chem-10-622-i012.jpg
13 R1 = TMS; R3 = H 76
14 R1 = Me; R3 = Me 98
15 graphic file with name Beilstein_J_Org_Chem-10-622-i013.jpg graphic file with name Beilstein_J_Org_Chem-10-622-i014.jpg 46

aIsolated yield based on complete consume of the starting material. bReaction conditions: substrate 1 (0.1 mmol), CBr4 (0.1 mmol), Ru(bpy)3Cl2 (5 mol %), dried CH3CN, blue LEDs (1 W), open to air. cRatio of the isomers in parentheses.