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. Author manuscript; available in PMC: 2019 May 9.
Published in final edited form as: J Am Chem Soc. 2018 Apr 25;140(18):5969–5975. doi: 10.1021/jacs.8b02535

Table 4.

Oxidative Coupling Using Various Halogen Blocking Groups

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Entry Conditionsa Halogenation results Coupling results
1 BnMe3NICl2, CaCO3, CH2Cl2/CH3OH, rt 70%, X= I 0% 1, 25% 16
2 NBS, CH2Cl2, rt 53%, X= Br 11% 1, 35% 16
3 NCS, DMF, 60 °C 4 h 44%, X= Cl 23% 1, 27% 16
4 Selectfluor®, CH3CN, rt 31%, X= F No reaction
a

Reaction conducted for 12 h unless specified otherwise.