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2005
C-C bond formation
O 0282
Synthesis of Medium-Ring and Iodinated Biaryl Compounds by Organocuprate
— A new functional-group-tolerant method for the intermolecular forma30- 046 Oxidation.
tion of sterically hindered biaryls as well as intramolecular formation of highly strained
medium-ring-containing biaryls is reported. It involves the iodine—magnesium exchange performed with aryl iodides, followed by conversion into organocuprates, and
final oxidation by use of new dinitrobenzene oxidant OXI. The intramolecular biaryl
formation allows cross-coupling of different aryl units by subsequent aminolysis of the
ring product with concomitant loss of the tether, as is exemplified by synthesis of compound (IX). The utility of the method is demonstrated by synthesis of ring core (XI) of
natural sanguiin H-5. — (SURRY, D. S.; SU, X.; FOX, D. J.; FRANCKEVICIUS, V.;
MACDONALD, S. J. F.; SPRING*, D. R.; Angew. Chem., Int. Ed. 44 (2005) 12,
1870-1873; Dep. Chem., Univ. Cambridge, Cambridge CB2 1EW, UK; Eng.) —
Klein
2005
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