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This reaction operates under mild conditions without requiring over\u2010stoichiometric amounts of metal terminal reductants. Excellent <jats:italic>Z\/E<\/jats:italic> ratios and good to excellent yields can be achieved for diverse and complex scaffolds with remarkable functional\u2010group compatibility. One potential utility of this reaction is demonstrated by the efficient synthesis of several <jats:italic>syn<\/jats:italic> homoallylic alcohols in a one\u2010pot two\u2010step sequence. Control experiments strongly support that the halogen\u2010atom transfer (XAT) process is the key to generating carbon radicals. DFT studies suggest that the catalytic system involves the Co(II)\/Co(III) cycle and the steric repulsion between the Co(II) catalyst, and the alkenyl radical in radical capture by Co(II) is the dominant factor controlling the <jats:italic>Z\/E<\/jats:italic> selectivity. 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