Organic Letters 2011-06-17

Preparation of functionalized organomanganese(II) reagents by direct insertion of manganese to aromatic and benzylic halides.

Zhihua Peng, Paul Knochel

Index: Org. Lett. 13(12) , 3198-201, (2011)

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Abstract

Functionalized arylmanganese compounds were prepared using commercial manganese powder in the presence of LiCl and catalytic amounts of both 2.5% InCl(3) and 2.5% PbCl(2) (THF, 0-50 °C). In addition, benzylic manganese reagents are obtained at 25 °C in ca. 70-80% yield (in the absence of LiCl) using commercial manganese powder and catalytic amounts of 2.5% InCl(3) and 2.5% PbCl(2). The resulting organomanganese reagents undergo smooth 1,2-addition, acylation, allylic substitution, Pd-catalyzed cross-coupling, and copper-catalyzed conjugate addition, affording the desired products in good yields.© 2011 American Chemical Society