Organic Letters
Letter
discussions. M.F. thanks NSERC, FRQNT, and NanoQAM
for generous funding.
Scheme 4. Proposed Mechanism and DFT-Calculated ΔGrx
(ΔHrx in Parentheses) for Each Step of the Catalytic Cycle
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We report herein a metal-free photoredox C−H functional-
ization of heteroarenes using an acridinium photocatalyst and
hypervalent iodine reagents under blue LED light. This light-
initiated chain reaction occurs under mild reaction conditions
and uses the broad and readily available carboxylic acid
monomer set. A range of functional groups are well tolerated
(olefins, alcohols, ethers, tertiary amines), and the method is
applicable to late-stage functionalization of complex molecules.
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ASSOCIATED CONTENT
* Supporting Information
The Supporting Information is available free of charge on the
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Full experimental details (PDF)
(10) For an early precedent of radical hydroxymethylation, see:
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2015, 137, 11340.
AUTHOR INFORMATION
Corresponding Authors
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ORCID
(12) Pitre, S. P.; McTiernan, C. D.; Vine, W.; DiPucchio, R.; Grenier,
M.; Scaiano, J. C. Sci. Rep. 2015, 5, 16397.
Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
We thank Dr. David Piotrowski (Pfizer), Dr. Joseph Tucker
(Pfizer), and Dr. Martins Oderinde (Pfizer) for helpful
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Org. Lett. XXXX, XXX, XXX−XXX