Organic transformations mediated by photoredox catalysis have been at the forefront of reaction discovery. Recently, it has been demonstrated that binuclear Au(I) bisphosphine complexes, such as [Au(μ-dppm)]X, are capable of mediating electron transfer to nonactivated bromoalkanes for the generation of a variety of alkyl radicals. The transfer reactions of bromine, derived from nonactivated bromoalkanes, are largely unknown. Therefore, we propose that unique metal-based mechanistic pathways are at play, as this binuclear gold catalyst has been known to produce Au(III) Lewis acid intermediates. The scope and proposed mechanistic overview for the formal bromine atom transfer reaction of nonactivated bromoalkanes mediated by photoredox Au(I) catalysis is presented. The methodology presented afforded good yields and a broad scope which include examples using bromoalkanes and iodoarenes.
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http://dx.doi.org/10.1021/acs.orglett.0c03030 | DOI Listing |
Org Lett
November 2020
Centre for Catalysis, Research and Innovation, Department of Chemistry and Biomolecular Sciences University of Ottawa Ottawa, Ontario K1N 6N5, Canada.
Organic transformations mediated by photoredox catalysis have been at the forefront of reaction discovery. Recently, it has been demonstrated that binuclear Au(I) bisphosphine complexes, such as [Au(μ-dppm)]X, are capable of mediating electron transfer to nonactivated bromoalkanes for the generation of a variety of alkyl radicals. The transfer reactions of bromine, derived from nonactivated bromoalkanes, are largely unknown.
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