We present the first example of visible-light-mediated multicomponent annulation of 1,7-diynes by taking advantage of quadruple cleavage olf carbon-halogen bonds of BrCCl to generate a C1 synthon, which was adeptly applied to the preparation of skeletally diverse 3-benzoyl-quinolin-2(1)-one acetates in moderate to good yields. Controlled experiments demonstrated that HO acted as both oxygen and hydrogen sources, and -dichlorovinyl carbonyl compound exhibited as a critical intermediate in this process. The mechanistic pathway involves Kharasch-type addition/6-exo-dig cyclization/1,5-(SN")-substitution/elimination/binucleophilic 1,6-addition/proton transfer/tautomerization sequence.
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| http://dx.doi.org/10.3390/molecules29040782 | DOI Listing |
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