Journal
CHEMICAL SCIENCE
Volume 7, Issue 7, Pages 4091-4100Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c5sc04709a
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Funding
- Gordon and Betty Moore Foundation
- NIH [NIGMS: R01 GM109194]
- National Institute of Health [F32GM116412]
- NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES [R01GM109194, F32GM116412] Funding Source: NIH RePORTER
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Photoinduced, copper-catalyzed cross-coupling can offer a complementary approach to thermal (non-photoinduced) methods for generating C-X (X = C, N, O, S, etc.) bonds. In this report, we describe the first detailed mechanistic investigation of one of the processes that we have developed, specifically, the (stoichiometric) coupling of a copper-thiolate with an aryl iodide. In particular, we focus on the chemistry of a discrete [Cu-I(SAr)(2)](-) complex (Ar = 2,6-dimethylphenyl), applying a range of techniques, including ESI-MS, cyclic voltammetry, transient luminescence spectroscopy, optical spectroscopy, DFT calculations, Stern-Volmer analysis, EPR spectroscopy, actinometry, and reactivity studies. The available data are consistent with the viability of a pathway in which photoexcited [Cu-I(SAr)(2)](-) * serves as an electron donor to an aryl iodide to afford an aryl radical, which then reacts in cage with the newly generated copper(II)-thiolate to furnish the cross-coupling product in a non-chain process.
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