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Three-step synthesis of end-substituted pentacenes.

Authors
Type
Published Article
Journal
The Journal of organic chemistry
Publication Date
Volume
72
Issue
25
Pages
9776–9778
Identifiers
PMID: 17999529
Source
Medline
License
Unknown

Abstract

A concise, three-step synthesis of 1,4,8,11-substituted 2,3,9,10-tetrakis(methoxycarbonyl)pentacenes from commercially available 1,2,4,5-tetrakis(bromomethyl)benzene was established. Efficient alkynylation, followed by formation of four fused rings via a zirconacyclopentadiene intermediate, and then oxidation with DDQ gave pentacenes 1a-c. The process was compatible with methyl, phenyl, and trimethylsilyl substituents, which have good solubility in various organic solvents.

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