Synthesis of Medium-Ring and Iodinated Biaryl Compounds by Organocuprate Oxidation

A biaryl banquet! Biphenyls with four ortho substituents, heteroaromatic compounds, iodinated biaryls, and medium rings containing biaryls are all readily synthesized by organocuprate oxidation. The utility of this new methodology is illustrated by the efficient synthesis of the medium‐ring core of...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2005-03, Vol.44 (12), p.1870-1873
Main Authors: Surry, David S., Su, Xianbin, Fox, David J., Franckevicius, Vilius, Macdonald, Simon J. F., Spring, David R.
Format: Article
Language:English
Subjects:
biaryls
Bridged Bicyclo Compounds - chemical synthesis
Bridged Bicyclo Compounds - chemistry
Copper - chemistry
CC coupling
Iodine - chemistry
medium-ring compounds
Molecular Structure
organocuprates
Organometallic Compounds - chemistry
oxidation
Oxidation-Reduction
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Summary:A biaryl banquet! Biphenyls with four ortho substituents, heteroaromatic compounds, iodinated biaryls, and medium rings containing biaryls are all readily synthesized by organocuprate oxidation. The utility of this new methodology is illustrated by the efficient synthesis of the medium‐ring core of sanguiin H‐5 (see scheme).
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200462642