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2Br; data from eMolecules database (eMolecules, Inc.), accessed via REAXYS (Elsevier, Inc.) on April 21, 2014.
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Co(Pc) reacted with benzyl mesylate to form benzyl radicals, quantitated as toluene (5, 4%) and bibenzyl (42%). See Table S1 in the ESI.†
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2O, 5 mol% dtbbpy, and 2 equiv. Zn dust in DMA (0.25 M) at 60°C for 10 min. BnBr is consumed, most of the iodobenzene remains.
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See ESI,† Scheme S1 and Chart S1-S10 for further selectivity and optimization details.
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For examples of stereoselective or stereospecific coupling of benzylic substrates, see ref 13j, k and m- p, and the references in the following endnote.
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Further study is needed to better understand reactions of secondary benzylic chlorides. For these electrophiles, a cocatalyst may not be required. In preliminary studies, reactions run without added Co(Pc) provided similar results to reactions run with Co(Pc). Unlike reactions with vinyl bromides (ref. 16), reactions with bis(oxazoline) ligands provided low yields of racemic material.
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