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Synlett 2003(5): 0585-0597
DOI: 10.1055/s-2003-38382
DOI: 10.1055/s-2003-38382
ACCOUNT
© Georg Thieme Verlag Stuttgart ˙ New York
Palladium-Catalyzed Intramolecular Arylation Reaction: Mechanism and Application for the Synthesis of Polyarenes
Antonio M. Echavarren*a, Berta Gómez-Lorb, Juan J. Gonzáleza, Óscar de Frutosaa Departamento de Química Orgánica, Universidad Autónoma de Madrid, Cantoblanco, 28049, Madrid, Spain
Fax: +34(913)973966; e-Mail: anton.echavarren@uam.es;
b Instituto de Ciencia de Materiales, CSIC, Cantoblanco, 28049, Madrid, Spain
Further Information
Publication History
Received
1 March 2002
Publication Date:
28 March 2003 (online)
Abstract
The intramolecular palladium-catalyzed reaction of aryl bromides and triflates with arenes has been used for the preparation of polyarenes. The synthesis of benz[e]acephenantrylenes, corannulenes, and C60H30, a ‘crushed fullerene’, by using this methodology are presented. Mechanistic studies on the arylation step point to an electrophilic substitution reaction pathway.
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1 Introduction
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2 An Approach to the Synthesis of Fullerene Fragments based on the Palladium-Catalyzed Arylation
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3 Synthesis of Benz[e]acephenantrylenes and Related
Polyarenes by Palladium-Catalyzed Arylation -
4 An Approach to the Synthesis of Dibenzocorannulene
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5 Mechanistic Insights into the Palladium-Catalyzed
Arylation Reaction -
5.1 The Role of Phosphine Ligands
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5.2 Electrophilic Substitution or C-H Activation?
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6 Palladium Catalyzed Arylation Synthesis of C 3 h Polyarenes from Truxenes
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7 Summary and Outlook
Key words
palladium - arylation - polyarenes - corannulenes - fullerene
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