A polarity-reversing radical cascade strategy for alkene di-functionalization by vicinal C-C and C-P bond-formation has been developed. This approach to concurrently adding phosphorous and a heteroarene across an olefin is enabled by photocatalytic generation of electrophilic P-centered radicals. Upon chemoselective addition to an olefin, the resulting nucleophilic C-centered radical selectively combines with electrophilic heteroarenes, such as pyridines. This multi-component coupling scheme for phosphinylalkylation complements classic two-component methods for hydrophosphinylation of alkenes and C-H phosphinylation of arenes. Included competition and photo-quenching experiments provide insight into the selectivity and mechanism of this polarity-reversal pathway.
A polarity-reversing radical cascade strategy for alkene di-functionalization by vicinal C-C and C-P bond-formation has been developed. This approach to concurrently adding pan class="Chemical">phosphorous and a heteroarene across an olefin is enabled by photocatalytic generation of electrophilic P-centered radicals. Upon chemoselective addition to an olefin, the resulting nucleophilic C-centered radical selectively combines with electrophilic heteroarenes, such as pyridines. This multi-component coupling scheme for phosphinylalkylation complements classic two-component methods for hydrophosphinylation of alkenes and C-H phosphinylation of arenes. Included competition and photo-quenching experiments provide insight into the selectivity and mechanism of this polarity-reversal pathway.
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