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. 2022 Aug 1;18:944–955. doi: 10.3762/bjoc.18.94

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Copyright © 2022, Fell et al.

This is an open access article licensed under the terms of the Beilstein-Institut Open Access License Agreement (https://www.beilstein-journals.org/bjoc/terms/terms), which is identical to the Creative Commons Attribution 4.0 International License (https://creativecommons.org/licenses/by/4.0). The reuse of material under this license requires that the author(s), source and license are credited. Third-party material in this article could be subject to other licenses (typically indicated in the credit line), and in this case, users are required to obtain permission from the license holder to reuse the material.

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Scheme 1 — Synthetic route from thiophene to 2,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dithieno[3,2-b:2’,3’-d]thiophene (26): a) Br₂, CHCl₃, rt, overnight, reflux, 4 h, 94% [33]; b) n-BuLi, −78 °C, 30 min, 1-formylpiperidine, anhydrous THF, −78 °C, then rt, overnight [15], 88%; c) ethyl thioglycolate, anhydrous potassium carbonate, anhydrous N,N-dimethylformamide, rt, 3 d, 83% [15]; d) 1 M aqueous lithium hydroxide, THF, 4 h, 94% [15]; e) copper powder, quinoline, 230 °C, 1 h, 81% [15]; f) N-bromosuccinimide, CHCl₃/glacial acetic acid, 0 °C, 1 h, rt, 1.5 h, 94% [15] ; g) n-BuLi, −90 °C, 20 min, triisopropyl borate, −80 °C, anhydrous THF, rt, overnight, 97% [34]; h) pinacol, toluene, 115 °C, 21.5 h, 79% [35].