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. Author manuscript; available in PMC: 2012 May 15.
Published in final edited form as: J Am Chem Soc. 2010 Nov 15;132(48):17092–17095. doi: 10.1021/ja1086547

Scheme 1.

Scheme 1

Orthogonal cross-coupling of benzoxasilole 7i. a

a Conditions: a. 7i (1 equiv), 3,5-dimethylphenylboronic acid (1.2 equiv), K2CO3 (2.5 equiv), Pd(PCy3)2Cl2 (2 mol %), THF/H2O, 65 °C; b. 4-iodoanisole (1.2 equiv), Pd(OAc)2 (4 mol %), dcpe (4.5 mol %), 2 M aq. NaOH (5 equiv), dioxane, 65 °C.