Efficient synthesis and structural characteristics of zwitterionic twisted π-electron system biaryls

Hu Kang; Antonio Facchetti; Charlotte L. Stern; Arnold L. Rheingold; W. Scott Kassel; Tobin J. Marks

doi:10.1021/ol051365x

Efficient synthesis and structural characteristics of zwitterionic twisted π-electron system biaryls

Hu Kang, Antonio Facchetti, Charlotte L. Stern, Arnold L. Rheingold, W. Scott Kassel, Tobin J. Marks^*

^*Corresponding author for this work

Chemistry

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

45 Scopus citations

Abstract

(Chemical Equation Presented) A series of unconventional twisted π-electron system molecules has been synthesized via Suzuki cross-coupling of two sterically hindered arenes. Crystallographic analysis of these molecules reveals a large ring-ring dihedral twist angle (87°) and a highly charge-separated zwitterionic ground state. An efficient conversion of phenols into aryl halides is also reported.

Original language	English (US)
Pages (from-to)	3721-3724
Number of pages	4
Journal	Organic Letters
Volume	7
Issue number	17
DOIs	https://doi.org/10.1021/ol051365x
State	Published - Aug 18 2005

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol051365x

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title = "Efficient synthesis and structural characteristics of zwitterionic twisted π-electron system biaryls",

abstract = "(Chemical Equation Presented) A series of unconventional twisted π-electron system molecules has been synthesized via Suzuki cross-coupling of two sterically hindered arenes. Crystallographic analysis of these molecules reveals a large ring-ring dihedral twist angle (87°) and a highly charge-separated zwitterionic ground state. An efficient conversion of phenols into aryl halides is also reported.",

author = "Hu Kang and Antonio Facchetti and Stern, \{Charlotte L.\} and Rheingold, \{Arnold L.\} and Kassel, \{W. Scott\} and Marks, \{Tobin J.\}",

year = "2005",

month = aug,

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doi = "10.1021/ol051365x",

language = "English (US)",

volume = "7",

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journal = "Organic Letters",

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T1 - Efficient synthesis and structural characteristics of zwitterionic twisted π-electron system biaryls

AU - Kang, Hu

AU - Facchetti, Antonio

AU - Stern, Charlotte L.

AU - Rheingold, Arnold L.

AU - Kassel, W. Scott

AU - Marks, Tobin J.

PY - 2005/8/18

Y1 - 2005/8/18

N2 - (Chemical Equation Presented) A series of unconventional twisted π-electron system molecules has been synthesized via Suzuki cross-coupling of two sterically hindered arenes. Crystallographic analysis of these molecules reveals a large ring-ring dihedral twist angle (87°) and a highly charge-separated zwitterionic ground state. An efficient conversion of phenols into aryl halides is also reported.

AB - (Chemical Equation Presented) A series of unconventional twisted π-electron system molecules has been synthesized via Suzuki cross-coupling of two sterically hindered arenes. Crystallographic analysis of these molecules reveals a large ring-ring dihedral twist angle (87°) and a highly charge-separated zwitterionic ground state. An efficient conversion of phenols into aryl halides is also reported.

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U2 - 10.1021/ol051365x

DO - 10.1021/ol051365x

M3 - Article

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JO - Organic Letters

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Efficient synthesis and structural characteristics of zwitterionic twisted π-electron system biaryls

Abstract

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CCDC 274102: Experimental Crystal Structure Determination

CCDC 274104: Experimental Crystal Structure Determination

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Efficient synthesis and structural characteristics of zwitterionic twisted π-electron system biaryls

Abstract

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CCDC 274102: Experimental Crystal Structure Determination

CCDC 274104: Experimental Crystal Structure Determination

Cite this