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“Golden” Cascade Cyclization to Benzo[ c ]‐Phenanthridines
Author(s) -
Hendrich Christoph M.,
Senn Sebastian,
Haas Lea,
Hoffmann Marvin T.,
Zschieschang Ute,
Greiner Luca C.,
Rominger Frank,
Rudolph Matthias,
Klauk Hagen,
Dreuw Andreas,
Hashmi A. Stephen K.
Publication year - 2021
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202102134
Subject(s) - domino , chemistry , cascade , cascade reaction , alkyne , combinatorial chemistry , cleavage (geology) , stereochemistry , catalysis , organic chemistry , materials science , chromatography , fracture (geology) , composite material
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.