Direct assembly of polyarenes via C-C coupling using PIFA/BF 3•Et2O

Enrico Faggi; Rosa M. Sebastián; Roser Pleixats; Adelina Vallribera; Alexandr Shafir; Alejandra Rodríguez-Gimeno; Carmen Ramírez De Arellano

doi:10.1021/ja107467c

Direct assembly of polyarenes via C-C coupling using PIFA/BF ₃•Et₂O

Enrico Faggi, Rosa M. Sebastián, Roser Pleixats, Adelina Vallribera, Alexandr Shafir, Alejandra Rodríguez-Gimeno, Carmen Ramírez De Arellano

Department of Chemistry

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

42 Citations (Scopus)

Abstract

Direct oxidative Kita-type coupling between naphthalene and substituted benzenes was found to proceed via four-component coupling, leading to a linear tetraarene with a binaphthalene core. The methodology was extendable to the coupling of unfunctionalized 1,1′-binaphthalene with mesitylene to give a linear hexaarene product in a remarkably chemoselective manner in 87% yield. The method represents an attractive alternative to the traditional syntheses of related oligonaphthalene products via a sequence of metal-catalyzed cross-coupling steps. © 2010 American Chemical Society.

Original language	English
Pages (from-to)	17980-17982
Journal	Journal of the American Chemical Society
Volume	132
Issue number	51
DOIs	https://doi.org/10.1021/ja107467c
Publication status	Published - 29 Dec 2010

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10.1021/ja107467c

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title = "Direct assembly of polyarenes via C-C coupling using PIFA/BF 3•Et2O",

abstract = "Direct oxidative Kita-type coupling between naphthalene and substituted benzenes was found to proceed via four-component coupling, leading to a linear tetraarene with a binaphthalene core. The methodology was extendable to the coupling of unfunctionalized 1,1′-binaphthalene with mesitylene to give a linear hexaarene product in a remarkably chemoselective manner in 87% yield. The method represents an attractive alternative to the traditional syntheses of related oligonaphthalene products via a sequence of metal-catalyzed cross-coupling steps. {\textcopyright} 2010 American Chemical Society.",

author = "Enrico Faggi and Sebasti{\'a}n, {Rosa M.} and Roser Pleixats and Adelina Vallribera and Alexandr Shafir and Alejandra Rodr{\'i}guez-Gimeno and {Ram{\'i}rez De Arellano}, Carmen",

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doi = "10.1021/ja107467c",

language = "English",

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Direct assembly of polyarenes via C-C coupling using PIFA/BF ₃•Et₂O. / Faggi, Enrico; Sebastián, Rosa M.; Pleixats, Roser ; Vallribera, Adelina; Shafir, Alexandr; Rodríguez-Gimeno, Alejandra; Ramírez De Arellano, Carmen.

In: Journal of the American Chemical Society, Vol. 132, No. 51, 29.12.2010, p. 17980-17982.

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

TY - JOUR

T1 - Direct assembly of polyarenes via C-C coupling using PIFA/BF 3•Et2O

AU - Faggi, Enrico

AU - Sebastián, Rosa M.

AU - Pleixats, Roser

AU - Vallribera, Adelina

AU - Shafir, Alexandr

AU - Rodríguez-Gimeno, Alejandra

AU - Ramírez De Arellano, Carmen

PY - 2010/12/29

Y1 - 2010/12/29

N2 - Direct oxidative Kita-type coupling between naphthalene and substituted benzenes was found to proceed via four-component coupling, leading to a linear tetraarene with a binaphthalene core. The methodology was extendable to the coupling of unfunctionalized 1,1′-binaphthalene with mesitylene to give a linear hexaarene product in a remarkably chemoselective manner in 87% yield. The method represents an attractive alternative to the traditional syntheses of related oligonaphthalene products via a sequence of metal-catalyzed cross-coupling steps. © 2010 American Chemical Society.

AB - Direct oxidative Kita-type coupling between naphthalene and substituted benzenes was found to proceed via four-component coupling, leading to a linear tetraarene with a binaphthalene core. The methodology was extendable to the coupling of unfunctionalized 1,1′-binaphthalene with mesitylene to give a linear hexaarene product in a remarkably chemoselective manner in 87% yield. The method represents an attractive alternative to the traditional syntheses of related oligonaphthalene products via a sequence of metal-catalyzed cross-coupling steps. © 2010 American Chemical Society.

U2 - 10.1021/ja107467c

DO - 10.1021/ja107467c

M3 - Article

VL - 132

SP - 17980

EP - 17982

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

SN - 0002-7863

IS - 51

ER -

Direct assembly of polyarenes via C-C coupling using PIFA/BF 3•Et2O

Abstract

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Direct assembly of polyarenes via C-C coupling using PIFA/BF ₃•Et₂O