Gold-Catalyzed Annulation of 1,8-Dialkynylnaphthalenes: Synthesis and Photoelectric Properties of Indenophenalene-Based Derivatives

Sara Tavakkoli Fard; Kohei Sekine; Kaveh Farshadfar; Frank Rominger; Matthias Rudolph; Alireza Ariafard; A. Stephen K. Hashmi

doi:10.1002/chem.202004846

Gold-Catalyzed Annulation of 1,8-Dialkynylnaphthalenes: Synthesis and Photoelectric Properties of Indenophenalene-Based Derivatives

Sara Tavakkoli Fard, Kohei Sekine, Kaveh Farshadfar, Frank Rominger, Matthias Rudolph, Alireza Ariafard^*, A. Stephen K. Hashmi^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

7 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	3552-3559
Number of pages	8
Journal	Chemistry - A European Journal
Volume	27
Issue number	10
DOIs	https://doi.org/10.1002/chem.202004846
Publication status	Published - 15 Feb 2021
Externally published	Yes

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title = "Gold-Catalyzed Annulation of 1,8-Dialkynylnaphthalenes: Synthesis and Photoelectric Properties of Indenophenalene-Based Derivatives",

abstract = "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.",

keywords = "alkynes, annulation, bidirectional synthesis, dual gold catalysis, extended π systems",

author = "Fard, \{Sara Tavakkoli\} and Kohei Sekine and Kaveh Farshadfar and Frank Rominger and Matthias Rudolph and Alireza Ariafard and Hashmi, \{A. Stephen K.\}",

note = "{\textcopyright} 2020 The Authors. ",

year = "2021",

month = feb,

day = "15",

doi = "10.1002/chem.202004846",

language = "English",

volume = "27",

pages = "3552--3559",

journal = "Chemistry - A European Journal",

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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.

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.

KW - alkynes

KW - annulation

KW - bidirectional synthesis

KW - dual gold catalysis

KW - extended π systems

UR - https://www.scopus.com/pages/publications/85100152443

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 -

Gold-Catalyzed Annulation of 1,8-Dialkynylnaphthalenes: Synthesis and Photoelectric Properties of Indenophenalene-Based Derivatives

Abstract

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