**4. Conclusions**

With the examples shown above, we could for the first time demonstrate the synthetic potential which can be harvested when combining the synthetic efficiency of electrooxidative dehydrogenative cross-coupling of ortho-substituted phenols with the power of Pd-catalyzed cross-coupling reactions. In our research it appeared necessary that the phenols are activated as nonaflates instead of triflates, as the latter showed considerable liabilities in the subsequent Pd-catalyzed reactions due to their hydrolytic lability against bases. In contrast, the nonaflates could be conveniently subjected to Pd-catalyzed cross-coupling reactions. The selectivity could be controlled by electronic and steric effects differentiating the reactivity of the two nonaflate groups. With the synthesis of a Bcl9 quateraryl mimetic, we could highlight this synthetic strategy on a particularly challenging substrate. The overall efficiency was shown in the highly convergent assembly of this quateraryl α-helix mimetic featuring the side chains of Bcl9. We expect that the synthetic methodology reported here will find applications in the synthesis of oligoarene structures, as required in Chemical Biology and Material Sciences.

**Supplementary Materials:** The following are available online at http://www.mdpi.com/2073-4344/10/3/340/s1, Experimental procedures and full spectroscopic characterization of all synthesized compounds.

**Author Contributions:** Conceptualization, M.V., S.R.W. and R.B.; development of the electrochemical coupling, B.D., M.V. and S.R.W.; synthesis of building blocks and oligoarene assembly, M.V., M.L., M.T. and M.H.H.; writing—original draft preparation, R.B.; structural assignment via NMR, H.W.; writing—review and editing, M.V., M.M.H. and S.R.W.; funding acquisition, S.R.W. and R.B. All authors have read and agreed to the published version of the manuscript.

**Funding:** This research was funded by the Austrian Science Fund (FWF) (Project I-2712) to R.B. and by the DFG (Wa1276/14-1) to S.R.W. as a joint D-A-CH project. Support for M.H.H. by the OeAD (Österreichischer Austauschdienst) via an Ernst-Mach-fellowship is gratefully acknowledged.

**Acknowledgments:** We thank Amber Ford and Sarah Berger for skillful assistance in the lab and for Open Access Funding by the Austrian Science Fund (FWF).

**Conflicts of Interest:** The authors declare no conflict of interest. The funders had no role in the design of the study; in the collection, analyses, or interpretation of data; in the writing of the manuscript, or in the decision to publish the results".
