Orthogonally functionalized naphthodithiophenes: Selective protection and borylation

Shoji Shinamura; Ryusuke Sugimoto; Naoyuki Yanai; Noriko Takemura; Tomoya Kashiki; Itaru Osaka; Eigo Miyazaki; Kazuo Takimiya

doi:10.1021/ol301797g

Orthogonally functionalized naphthodithiophenes: Selective protection and borylation

Shoji Shinamura, Ryusuke Sugimoto, Naoyuki Yanai, Noriko Takemura, Tomoya Kashiki, Itaru Osaka, Eigo Miyazaki, Kazuo Takimiya

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

40 Citations (Scopus)

Abstract

Selective functionalization protocols of naphtho[1,2-b;5,6-b′] dithiophene (NDT3) by combining protection of the thiophene r-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.

Original language	English
Pages (from-to)	4718-4721
Number of pages	4
Journal	Organic letters
Volume	14
Issue number	18
DOIs	https://doi.org/10.1021/ol301797g
Publication status	Published - 2012 Sept 21
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol301797g

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AU - Shinamura, Shoji

AU - Sugimoto, Ryusuke

AU - Yanai, Naoyuki

AU - Takemura, Noriko

AU - Kashiki, Tomoya

AU - Osaka, Itaru

AU - Miyazaki, Eigo

AU - Takimiya, Kazuo

PY - 2012/9/21

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AB - Selective functionalization protocols of naphtho[1,2-b;5,6-b′] dithiophene (NDT3) by combining protection of the thiophene r-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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Orthogonally functionalized naphthodithiophenes: Selective protection and borylation

Abstract

ASJC Scopus subject areas

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