Synlett 2011(14): 1951-1955  
DOI: 10.1055/s-0030-1260941
SYNPACTS
© Georg Thieme Verlag Stuttgart ˙ New York

No Detours: Palladium-Catalyzed Oxidative C-H/C-H Cross-Couplings of Heteroarenes

Wei Han, Armin R. Ofial*
Department Chemie, Ludwig-Maximilians-Universität München, Butenandtstr. 5-13 (Haus F), 81377 München, Germany
Fax: +49(89)21809977715; e-Mail: ofial@lmu.de;
Further Information

Publication History

Received 20 May 2011
Publication Date:
03 August 2011 (online)

Abstract

Recent developments in the field of intermolecular cross-couplings between heteroarenes through dual C-H bond cleavage under oxidative conditions are reviewed. The use of palladium catalysts allows for regioselective carbon-carbon bond formations between important classes of heteroarenes without the need to prefunctionalize the positions that shall be linked.

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23

The presence of Ag+ ions also affects the selectivity for the cross-coupling reaction. As investigated in detail for the reaction of benzothiazole with 4,5-dimethylthiazole, the cross-coupling is strongly favored (92% yield) in the presence of AgF (2 equiv; Scheme  [8] ). Without AgF but under otherwise identical reaction conditions, a mixture of the cross-coupling product (41%) and both homodimers, i.e., bi(4,5-dimethyl)thiazolyl (43%) and bi(benzothiazolyl) (15%) were produced.