Straightforward and regiospecific synthesis of 1,3,5,7-tetra-arylated acene bearing different aryl groups

Sato, Ryota; Chen, Kunfeng; Yasuda, Takeshi; Kanbara, Takaki; Kuwabara, Junpei

doi:10.1039/d3qo00289f

Cited by 2 publications

(2 citation statements)

References 40 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…To address these issues, we hypothesized that the steric effect of the aryl groups initially introduced at the 1,5-positions would allow the regioselective introduction of aryl groups at the 3-and 7-positions in the second CDC reaction (Scheme 14). [88] In this strategy, the readily available 1,5-dibromonaphthalene can be used as the starting material for the introduction of aryl groups by conventional crosscoupling reactions. To prove this concept, xylyl, pentafluorophenyl, and diarylamino groups were introduced at the 1,5positions of naphthalene using the Suzuki-Miyaura crosscoupling, direct arylation, and the Buchwald-Hartwig reaction, respectively.…”

Section: Synthesis Of Tetraarylated Acenes By a Combination Of Conven...mentioning

confidence: 99%

See 1 more Smart Citation

Synthesis of Organic Optoelectronic Materials Using Direct C−H Functionalization

Kuwabara,

Kanbara

2023

ChemPlusChem

Self Cite

View full text Add to dashboard Cite

Small molecules and polymers with conjugated structures can be used as organic optoelectronic materials. These molecules have conventionally been synthesized by cross‐coupling reactions; however, in recent years, direct functionalization of C‐H bonds has been used to synthesize organic optoelectronic materials. Representative reactions include direct arylation reactions (C‐H/C‐X couplings, with X being halogen or pseudo‐halogen) and cross‐dehydrogenative coupling (C‐H/C‐H cross‐coupling) reactions. Although these reactions are convenient for short‐step synthesis, they require regioselectivity in the C‐H bonds and suppression of undesired homo‐coupling side reactions. This review introduces examples of the synthesis of organic optoelectronic materials using two types of direct C‐H functionalization reactions. In addition, we summarize our recent activities in the development of direct C‐H functionalization reactions using fluorobenzenes as substrates. This review covers the reaction mechanism and material properties of the resulting products.

show abstract

Section: Synthesis Of Tetraarylated Acenes By a Combination Of Conven...mentioning

confidence: 99%

“…Synthesis of 1,3,5,7-tetraarylated acene bearing different aryl groups via conventional cross coupling reaction and CDC reactions. [88] Redrawn from ref. [88] Copyright (2023), with permission from RSC.…”

Section: Conflict Of Interestsmentioning

confidence: 99%

Synthesis of Organic Optoelectronic Materials Using Direct C−H Functionalization

Kuwabara,

Kanbara

2023

ChemPlusChem

Self Cite

View full text Add to dashboard Cite

show abstract

Mechanistic study on the reductive elimination of (aryl)(fluoroaryl)palladium complexes: a key step in regiospecific dehydrogenative cross-coupling

Iida,

Sato,

Yoshigoe

et al. 2024

Dalton Trans.

View full text Add to dashboard Cite

show abstract

Straightforward and regiospecific synthesis of 1,3,5,7-tetra-arylated acene bearing different aryl groups

Abstract: 1,3,5,7-Tetra-arylated acene derivatives were synthesised by first introducing aryl groups at the 1,5-positions via cross-coupling reactions and then selectively introducing pentafluorophenyl groups at the 3,7-positions via CDC reactions.

Cited by 2 publications

References 40 publications

Synthesis of Organic Optoelectronic Materials Using Direct C−H Functionalization

Synthesis of Organic Optoelectronic Materials Using Direct C−H Functionalization

Mechanistic study on the reductive elimination of (aryl)(fluoroaryl)palladium complexes: a key step in regiospecific dehydrogenative cross-coupling

Contact Info

Product

Resources

About