TY - JOUR
T1 - Gold-Catalyzed Annulation of 1,8-Dialkynylnaphthalenes
T2 - Synthesis and Photoelectric Properties of Indenophenalene-Based Derivatives
AU - Fard, Sara Tavakkoli
AU - Sekine, Kohei
AU - Farshadfar, Kaveh
AU - Rominger, Frank
AU - Rudolph, Matthias
AU - Ariafard, Alireza
AU - Hashmi, A. Stephen K.
N1 - Funding Information:
S.T.F. is grateful for Ph.D funding from the Hans‐Böckler‐Stiftung. We gratefully acknowledge the generous allocation of computing time from the Australian National Computational Infrastructure and University of Tasmania, and the Australian Research Council (grant number DP180100904) for financial support. Open access funding enabled and organized by Projekt DEAL.
Publisher Copyright:
© 2020 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH
PY - 2021/2/15
Y1 - 2021/2/15
N2 - A simple gold-catalyzed annulation of 1,8-dialkynylnaphthalenes utilizing a cationic gold catalyst was developed. Such a peri-position of two alkynyl substituents has not been studied in gold catalysis before. Dependent on the substrate, the reactions either follow a mechanism involving vinyl cation intermediates or involve a dual gold catalysis mechanism which in an initial 6-endo-dig-cyclization generates gold(I) vinylidene intermediates that are able to insert into C−H bonds. Indenophenalene derivatives were obtained in moderate to high yields. In addition, the bidirectional gold-catalyzed annulation of tetraynes provided even larger conjugated π-systems. The optoelectronic properties of the products were also investigated.
AB - A simple gold-catalyzed annulation of 1,8-dialkynylnaphthalenes utilizing a cationic gold catalyst was developed. Such a peri-position of two alkynyl substituents has not been studied in gold catalysis before. Dependent on the substrate, the reactions either follow a mechanism involving vinyl cation intermediates or involve a dual gold catalysis mechanism which in an initial 6-endo-dig-cyclization generates gold(I) vinylidene intermediates that are able to insert into C−H bonds. Indenophenalene derivatives were obtained in moderate to high yields. In addition, the bidirectional gold-catalyzed annulation of tetraynes provided even larger conjugated π-systems. The optoelectronic properties of the products were also investigated.
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U2 - 10.1002/chem.202004846
DO - 10.1002/chem.202004846
M3 - Article
C2 - 33210327
AN - SCOPUS:85100152443
SN - 0947-6539
VL - 27
SP - 3552
EP - 3559
JO - Chemistry - A European Journal
JF - Chemistry - A European Journal
IS - 10
ER -