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. Author manuscript; available in PMC: 2013 Sep 7.
Published in final edited form as: Org Lett. 2012 Aug 15;14(17):4606–4609. doi: 10.1021/ol302063g

Scheme 6.

Scheme 6

One pot lithium-halogen exchange, borylation, and SCM reaction of heteroarenes.

Reaction conditions: ArX (0.75 mmol, 3.0 equiv), THF (1.0 mL), n-BuLi (2.5m in hexanes, 0.83 mmol, 3.3 equiv), B(OiPr)3 (0.83 mmol, 3.3 equiv), −78 °C, 1 h, K3PO4 aq (0.5 m, 2.0 mL), ArX (0.25 mmol, 1.0 equiv), 13 (3 mol %), 2 h, 40 °C. Isolated yields are the average of two runs. (a) The reaction was run for 5 h instead of 2 h.