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note
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In the absence of the iron catalyst, no reaction was observed for 2-chlorobenzophenone.
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note
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We submitted the substituted iodoesters 3g-i to Pd-and Ni-catalyzed cross-coupling and found that in the case of Pd catalysis, 4-iodoester 3i reacts significantly faster than 3g and 3h, whereas under Ni catalysis, the 3-iodoester 3h is the fastest. These results indicate that the mechanism of Ni-, Pd- and Fe-catalyzed cross-coupling reactions is significantly different, as electronic and steric effects of the substituents affect them differently (see Supporting Information for details).
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Interestingly, copper reagents made from aryl lithium species can also be used. The reaction proceeds at a similar rate (somewhat faster). The occurrence of an I-Cu exchange reaction is minimized with this type of copper species (ArCu(CN)Li).
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note
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A patent application for this and related crossing-coupling reactions has been filed.
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