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

Research output: Contribution to journalArticle

41 Citations (Scopus)

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 languageEnglish
Pages (from-to)3721-3724
Number of pages4
JournalOrganic Letters
Volume7
Issue number17
DOIs
Publication statusPublished - Aug 18 2005

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Phenols
Electrons
Molecules
rings
cross coupling
Dihedral angle
synthesis
phenols
Ground state
halides
dihedral angle
molecules
electrons
ground state

ASJC Scopus subject areas

  • Molecular Medicine

Cite this

Efficient synthesis and structural characteristics of zwitterionic twisted π-electron system biaryls. / Kang, Hu; Facchetti, Antonio; Stern, Charlotte L.; Rheingold, Arnold L.; Kassel, W. Scott; Marks, Tobin J.

In: Organic Letters, Vol. 7, No. 17, 18.08.2005, p. 3721-3724.

Research output: Contribution to journalArticle

Kang, Hu ; Facchetti, Antonio ; Stern, Charlotte L. ; Rheingold, Arnold L. ; Kassel, W. Scott ; Marks, Tobin J. / Efficient synthesis and structural characteristics of zwitterionic twisted π-electron system biaryls. In: Organic Letters. 2005 ; Vol. 7, No. 17. pp. 3721-3724.
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