38691-00-8Relevant articles and documents
α-Arylation by rearrangement: On the reaction of enolates with diaryliodonium salts
Norrby, Per-Ola,Petersen, Tue B.,Bielawski, Marcin,Olofsson, Berit
, p. 8251 - 8254 (2010)
Surprising equilibration: A new mechanism for the title reaction is supported by DFT calculations and experimental observations. The C-I and OI intermediates are isoenergetic and equilibrate quickly. Thus, any chiral information induced in the initial complex will be destroyed. In the final CC bond-forming step, a [2,3]-rearrangement from the O-I bonded intermediate is slightly preferred over the [1,2]elimination from the C-I bonded isomer (see scheme). (Figure Presented)
Electrochemical-Induced Ring Transformation of Cyclic α-(ortho-Iodophenyl)-β-oxoesters
Strehl, Julia,Kahrs, Christoph,Müller, Thomas,Hilt, Gerhard,Christoffers, Jens
, p. 3222 - 3225 (2020/02/11)
Cyclic α-(ortho-iodophenyl)-β-oxoesters were converted in a ring-expanding transformation to furnish benzannulated cycloalkanone carboxylic esters. The reaction sequence started by electrochemical reduction of the iodoarene moiety. In a mechanistic rationale, the resulting carbanionic species was adding to the carbonyl group under formation of a strained, tricyclic benzocyclobutene intermediate, which underwent carbon–carbon bond cleavage and rearrangement of the carbon skeleton by retro-aldol reaction. The scope of the reaction sequence was investigated by converting cyclic oxoesters with different ring sizes yielding benzocycloheptanone, -nonanone and -decanone derivatives in moderate to good yields. Furthermore, acyclic starting materials and cyclic compounds carrying additional substituents on the iodophenyl ring were submitted to this reaction sequence. The starting materials for this transformation are straightforwardly obtained by conversion of β-oxoesters with phenyliodobis(trifluoroacetate).
Tandem one-pot construction of indoles via palladium and copper-catalyzed coupling reactions of the blaise reaction intermediate
Kim, Ju Hyun,Lee, Sang-Gi
scheme or table, p. 1464 - 1476 (2012/09/08)
The palladium-catalyzed intramolecular N-arylation of the Blaise reaction intermediate, formed by reaction of nitriles with an in situ generated Reformatsky reagent from ethyl -bromo - (2-bromophenyl)acetate and zinc, afforded indoles in good yields. Exte
Sulfoxide-mediated α-arylation of carbonyl compounds
Huang, Xueliang,Maulide, Nuno
, p. 8510 - 8513 (2011/07/09)
A novel sulfoxide-mediated α-arylation of carbonyl compounds is reported. This reaction proceeds under very mild conditions at room temperature and does not require any transition-metal promoter or catalyst.
