Synthesis of arylated perylene bisimides through C - H bond cleavage under ruthenium catalysis

Satomi Nakazono; Shanmugam Easwaramoorthi; Dongho Kim; Hiroshi Shinokubo; Atsuhiro Osuka

doi:10.1021/ol902271b

Synthesis of arylated perylene bisimides through C - H bond cleavage under ruthenium catalysis

Satomi Nakazono, Shanmugam Easwaramoorthi, Dongho Kim, Hiroshi Shinokubo, Atsuhiro Osuka

Department of Chemistry

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

121 Citations (Scopus)

Abstract

"Chemical Equation Presented" Treatment of perylene bisimide (PBI) with various arylboronates in the presence of a ruthenium catalyst provides tetraarylated PBIs at 2,5,8,11-positions In good yields with perfect regioselectlvity. The electronic nature of the Introduced aryl substltuents has a significant Impact on their optical and electronic properties. This protocol has been applied to the synthesis of a water-soluble emissive PBI derivative.

Original language	English
Pages (from-to)	5426-5429
Number of pages	4
Journal	Organic Letters
Volume	11
Issue number	23
DOIs	https://doi.org/10.1021/ol902271b
Publication status	Published - 2009 Dec 3

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol902271b

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abstract = "{"}Chemical Equation Presented{"} Treatment of perylene bisimide (PBI) with various arylboronates in the presence of a ruthenium catalyst provides tetraarylated PBIs at 2,5,8,11-positions In good yields with perfect regioselectlvity. The electronic nature of the Introduced aryl substltuents has a significant Impact on their optical and electronic properties. This protocol has been applied to the synthesis of a water-soluble emissive PBI derivative.",

author = "Satomi Nakazono and Shanmugam Easwaramoorthi and Dongho Kim and Hiroshi Shinokubo and Atsuhiro Osuka",

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AU - Nakazono, Satomi

AU - Easwaramoorthi, Shanmugam

AU - Kim, Dongho

AU - Shinokubo, Hiroshi

AU - Osuka, Atsuhiro

PY - 2009/12/3

Y1 - 2009/12/3

N2 - "Chemical Equation Presented" Treatment of perylene bisimide (PBI) with various arylboronates in the presence of a ruthenium catalyst provides tetraarylated PBIs at 2,5,8,11-positions In good yields with perfect regioselectlvity. The electronic nature of the Introduced aryl substltuents has a significant Impact on their optical and electronic properties. This protocol has been applied to the synthesis of a water-soluble emissive PBI derivative.

AB - "Chemical Equation Presented" Treatment of perylene bisimide (PBI) with various arylboronates in the presence of a ruthenium catalyst provides tetraarylated PBIs at 2,5,8,11-positions In good yields with perfect regioselectlvity. The electronic nature of the Introduced aryl substltuents has a significant Impact on their optical and electronic properties. This protocol has been applied to the synthesis of a water-soluble emissive PBI derivative.

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JO - Organic Letters

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Synthesis of arylated perylene bisimides through C - H bond cleavage under ruthenium catalysis

Abstract

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