1,{3|three},2-diazaphospholenes hydrides (DAP-Hs) are {highly|extremely|very|hugely} nucleophilic organic hydrides serving as main-group catalysts {for a|to get a|for any} {range|variety} of {attractive|appealing|desirable|eye-catching} transformations. DAP hydrides can act as stoichiometric hydrogen atom transfer agents in radical reactions. Herein, we report a DAP-catalyzed reductive radical cyclization of a broad {range|variety} of aryl and alkyl halides {under|below|beneath} mild {conditions|circumstances|situations}. The pivotal DAP catalyst turnover was {achieved|accomplished} by a DBU-assisted σ-bond metathesis {between|in between|among|amongst|involving} the formed DAP halide and HBpin {rapidly|quickly|swiftly} regenerating DAP H. The transformation is {significantly|considerably|substantially|drastically} accelerated by irradiation with visible light. Mechanistic investigations indicate that visible light irradiation {leads to|results in} the formation of DAP dimers {which are|that are} in equilibrium {with the|using the|with all the|together with the} DAP radicals accelerating the cyclization. The direct use of (DAP){2|two} enabled a catalytic protocol {in the|within the|inside the} absence of light. 5,7-Dibromoquinoline Chemscene Benzene-1,2,4,5-tetraol web PMID:24455443
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