Organisch-Chemisches Institut, Heidelberg University, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.
Interdisciplinary Center for Scientific Computing (IWR), Heidelberg University, Im Neuenheimer Feld 205 A, 69120, Heidelberg, Germany.
Chemistry. 2021 Oct 21;27(59):14778-14784. doi: 10.1002/chem.202102134. Epub 2021 Sep 12.
Herein, we describe a gold-catalyzed cascade cyclization of Boc-protected benzylamines bearing two tethered alkyne moieties in a domino reaction initiated by a 6-endo-dig cyclization. The reaction was screened intensively, and the scope was explored, resulting in nine new Boc-protected dihydrobenzo[c]phenanthridines with yields of up to 98 %; even a π-extension and two bidirectional approaches were successful. Furthermore, thermal cleavage of the Boc group and subsequent oxidation gave substituted benzo[c]phenanthridines in up to quantitative yields. Two bidirectional approaches under the optimized conditions were successful, and the resulting π-extended molecules were tested as organic semiconductors in organic thin-film transistors.
在此，我们描述了一种 Boc 保护的苄胺在金催化下的级联环化反应，该反应具有两个桥连炔基部分，通过 6-endo-dig 环化引发了多米诺反应。我们对反应进行了深入筛选，并对其范围进行了探索，得到了 9 个新的 Boc 保护的二氢苯并[c]菲啶，产率高达 98%；甚至π-扩展和两种双向方法都取得了成功。此外，Boc 基团的热裂解和随后的氧化以高达定量的产率得到取代的苯并[c]菲啶。在优化条件下，两种双向方法都取得了成功，所得的π扩展分子被测试为有机薄膜晶体管中的有机半导体。
