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. 2005 Aug 18;7(17):3721-4.
doi: 10.1021/ol051365x.

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

Hu Kang  1 , Antonio Facchetti, Charlotte L Stern, Arnold L Rheingold, W Scott Kassel, Tobin J Marks
Affiliations

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

Hu Kang et al. Org Lett. .

Abstract

A series of unconventional twisted pi-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 degrees ) and a highly charge-separated zwitterionic ground state. An efficient conversion of phenols into aryl halides is also reported. [reaction: see text]

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