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- W1968018818 abstract "The CoH3(PPh3)3 catalyzed addition reaction between azobenzenes and internal alkynes produces 2-stilbenylazobenzenes and isomeric 2,3-dihydrocinnolines which are intermediates in the rhodium catalyzed formation of N-anilinoindoles from the same substrates. The structures of six adducts were resolved by single crystal X-ray structural analyses. In both reactions the insertion of the alkyne into a M–H bond and ortho-metalation of the 1,2-diazene are key steps of the catalytic cycle. When only one phenyl ring of the diazene is substituted like in 3,5-dichloro- and 3,5-difluoroazobenzene, selectively this ring is ortho-metalated in the case of cobalt while only the unsubstituted or both rings are attacked in rhodium catalysis. This difference enables a two-step regioselective cobalt catalyzed synthesis of the corresponding N-anilinoindole via isolation of 2-stilbenyl-3,5-difluoroazobenzene and subsequent acid catalyzed rearrangement to the indole derivative. Results obtained with 4-methoxytolan reveal that insertion into the Co–H bond produces regioisomers the ratio of which is determined by the sign of the triple bond polarization. It is postulated that insertion initially affords a cis-alkenyl ligand which undergoes an efficient cis–trans isomerization except when decafluorotolan is the alkyne; in this case also the cis-alkenyl product was isolated. Catalytic amounts of HOAc lead to a tenfold increase of reaction rate. No reaction is observed when sterically demanding substitutents like mesityl and adamantyl are introduced to the triple bond." @default.
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- W1968018818 date "1998-05-01" @default.
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- W1968018818 title "Transition metal complexes of diazenes XLI: cobalt catalyzed addition of internal alkynes to 1,2-diaryldiazenes: formation of 2,3-dihydrocinnolines, mono- and distilbenylazobenzenes" @default.
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- W1968018818 doi "https://doi.org/10.1016/s0022-328x(98)00404-5" @default.
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