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. Author manuscript; available in PMC: 2012 Mar 29.
Published in final edited form as: Org Lett. 2010 Mar 19;12(6):1160–1163. doi: 10.1021/ol902836c

Figure 3.

Figure 3

(a) The conditions shown in entry 10 used Li sticks/KOt-Bu and (PhSe)2 to afford 8 in an isolated yield of 91% yield. (b) Utility of this oxidative cyclization is demonstrated in the syntheses of cyclic secondary amines 9–13 (P = Boc). (c) Synthesis of ionophore 2 featuring an oxidative C-N bond forming cyclization and either a Sandmeyer-like reaction (+CuOAc) or a metal-free aminoarylation (−CuOAc) with a secondary amine. (d) Utility of these aminoarylation conditions used in Figure 2c is demonstrated in the synthesis of tertiary arylamines 16–22. Footnotes: aDetermined by LCMS. Isolated yield shown in parenthesis. bMajor product was a dimer. cStarting material recovered. dMajor product was an alkene. eMajor product was an alkane. fFirst/second values rerpresent the % yield obtained with/without CuOAc (cat).