Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 354, Issue 18, Pages 3517-3522Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201200738
Keywords
C?H activation; diaryliodonium salts; palladium; photochemistry; radicals
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Funding
- NIH NIGMS [GM073836]
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This paper describes a photoredox palladium/iridium-catalyzed C?H arylation with diaryliodonium reagents. Details of the reaction optimization, substrate scope, and mechanism are presented along with a comparison to a related method in which aryldiazonium salts are used in place of diaryliodonium reagents. The unprecedentedly mild reaction conditions (25?degrees C in methanol), the requirement for light and a photocatalyst, the inhibitory effect of radical scavengers, and the observed chemoselectivity trends are all consistent with a radical-mediated mechanism for this transformation. This stands in contrast to the analogous thermal reaction with diaryliodonium reagents that is believed to proceed via an ionic 2e- pathway and requires a much higher reaction temperature (100?degrees C).
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