Orthogonally Functionalized Naphthodithiophenes: Selective Protection and Borylation

Orthogonally Functionalized Naphthodithiophenes: Selective Protection and Borylation

Selective functionalization protocols of naphtho[1,2-b;5,6-b′]dithiophene (NDT3) by combining protection of the thiophene α-positions and direct borylation on the naphthalene core are described, which allows synthesizing a number of new NDT3-based building blocks with various substituents and isomer...

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Bibliographic Details
Published in:Organic letters Vol. 14; no. 18; pp. 4718 - 4721
Main Authors: Shinamura, Shoji, Sugimoto, Ryusuke, Yanai, Naoyuki, Takemura, Noriko, Kashiki, Tomoya, Osaka, Itaru, Miyazaki, Eigo, Takimiya, Kazuo
Format: Journal Article
Language:English
Published: United States American Chemical Society 21-09-2012
Online Access:Get full text
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Summary:Selective functionalization protocols of naphtho[1,2-b;5,6-b′]dithiophene (NDT3) by combining protection of the thiophene α-positions and direct borylation on the naphthalene core are described, which allows synthesizing a number of new NDT3-based building blocks with various substituents and isomeric NDT3-based polymers with different main chain structures. The same protocol is applicable to other isomeric naphthodithiophenes (NDTs), which affords a set of key building blocks for the development of elaborated functional π-materials.
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol301797g