"Golden" Cascade Cyclization to Benzo[c]-Phenanthridines.

Autor: Hendrich CM; Organisch-Chemisches Institut, Heidelberg University, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany., Senn S; Organisch-Chemisches Institut, Heidelberg University, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany., Haas L; Organisch-Chemisches Institut, Heidelberg University, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany., Hoffmann MT; Interdisciplinary Center for Scientific Computing (IWR), Heidelberg University, Im Neuenheimer Feld 205 A, 69120, Heidelberg, Germany., Zschieschang U; Max Planck Institute for Solid State Research, Heisenbergstr. 1, 70569, Stuttgart, Germany., Greiner LC; Organisch-Chemisches Institut, Heidelberg University, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany., Rominger F; Organisch-Chemisches Institut, Heidelberg University, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany., Rudolph M; Organisch-Chemisches Institut, Heidelberg University, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany., Klauk H; Max Planck Institute for Solid State Research, Heisenbergstr. 1, 70569, Stuttgart, Germany., Dreuw A; Interdisciplinary Center for Scientific Computing (IWR), Heidelberg University, Im Neuenheimer Feld 205 A, 69120, Heidelberg, Germany., Hashmi ASK; Organisch-Chemisches Institut, Heidelberg University, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.
Jazyk: angličtina
Zdroj: Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2021 Oct 21; Vol. 27 (59), pp. 14778-14784. Date of Electronic Publication: 2021 Sep 12.
DOI: 10.1002/chem.202102134
Abstrakt: 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.
(© 2021 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.)
Databáze: MEDLINE
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