187741-66-8Relevant academic research and scientific papers
Rapid assembly of tetrahydrodibenzofurans and tetrahydrocarbazoles from benzene and o-iodophenols and o-iodoanilines: Reductive radical arylation of benzene in action
Crich, David,Sannigrahi, Mousumi
, p. 3319 - 3322 (2002)
In the presence of catalytic benzeneselenol, generated in situ from diphenyl diselenide, tributyltin hydride brings about the radical addition of ortho-functionalized aryl iodides to benzene giving aryl cyclohexadienes. These may then be cyclized by means of standard electrophilic reagents. The use of o-methoxycarbamoyliodobenzene leads to a tetrahydrocarbazole, whereas o-iodobenzoic acid provides a tetrahydrodibenzopyranone. o-Iodophenols lead, overall, to tetrahydrodibenzofurans.
Synthesis of functionalized carbamates through a palladium-catalyzed reductive carbonylation of substituted nitrobenzenes
Wchman, Petra,Borst, Leo,Kamer, Paul C. J.,Van Leeuwen, Piet W. N. M.
, p. 13 - 21 (2007/10/03)
The palladium-catalyzed reductive carbonylation of ortho and para-substituted nitrobenzenes has proven to be an attractive route for the synthesis of functionalized carbamates. For the Pd(1,10-phenanthroline)2(triilate}2 catalyst system, the scope of the reaction has been studied. Substrates with electron-donating substituents at the para position were found to decrease the catalytic activity, most probably as a result of their relatively low oxidizing capacity. The selectivity towards the desired carbamate, however, was increased for these substrates. Under the influence of electron-withdrawing substituents the azoxybenzene and azobenzene derivatives became important side products. Introduction of large steric hindrance at the ortho position of the nitro substrates gave rise to an interesting side reaction, viz. methoxylation of the aromatic ring. The methoxylation reaction appeared to occur on an intermediate species in the catalytic cycle. Several functionalities have shown to be resistant to the reaction conditions required for the conversion of the nitro group. Especially with 4-nitrobenzoic acid, an extremely high activity and selectivity was found, thus yielding a very convenient synthesis for N-protected amines containing carboxylic acid functions. VCH Verlagsgesellschaft mbH.
