A Convenient Couple

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Science  08 Sep 2006:
Vol. 313, Issue 5792, pp. 1364
DOI: 10.1126/science.313.5792.1364b

Biaryls are a common structural motif in pharmaceutically important compounds and have traditionally been prepared using strategies that couple a halogenated substrate to a second compound pre-adorned with a reactive group such as a boronic ester or alkyl stannane. Recent research has focused on improving the efficiency of these syntheses by linking aryl halides directly to the aromatic C-H bond of a partner ring. Yanagisawa et al. extend this trend with a rhodium catalyst that couples iodobenzene and its derivatives efficiently to heterocyclic aromatics, including substituted thiophenes, furans, and pyrroles. At 3 mole % loading, the catalyst induces regioselective bond formation at the carbon adjacent to an oxygen or sulfur atom, though somewhat surprisingly selects for the 3 position in N-substituted 1-phenylpyrrole. Pi-accepting bulky phosphite ligands played a crucial role in achieving catalytic efficiency and also conferred air stability on the Rh complex. The catalyst proved capable of coupling aryl halides to methoxy-substituted benzenes as well, albeit with diminished regioselectivities relative to those obtained with the heterocyclic substrates. — JSY

J. Am. Chem. Soc. 128, 10.1021/ja064500p (2006).

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