Branch-Selective Alkene Hydroarylation by Cooperative Destabilization: Iridium-Catalyzed ortho-Alkylation of Acetanilides
نویسندگان
چکیده
An iridium(I) catalyst system, modified with the wide-bite-angle and electron-deficient bisphosphine d(F) ppb (1,4-bis(di(pentafluorophenyl)phosphino)butane) promotes highly branch-selective hydroarylation reactions between diverse acetanilides and aryl- or alkyl-substituted alkenes. This provides direct and ortho-selective access to synthetically challenging anilines, and addresses long-standing issues associated with related Friedel-Crafts alkylations.
منابع مشابه
Enantioselective intramolecular hydroarylation of alkenes via directed C-H bond activation.
Highly enantioselective catalytic intramolecular ortho-alkylation of aromatic imines containing alkenyl groups tethered at the meta position relative to the imine directing group has been achieved using [RhCl(coe)2]2 and chiral phosphoramidite ligands. Cyclization of substrates containing 1,1- and 1,2-disubstituted as well as trisubstituted alkenes were achieved with enantioselectivities >90% e...
متن کاملIridium-catalyzed regio- and enantioselective allylic alkylation of fluorobis(phenylsulfonyl)methane.
Highly regio- and enantioselective allylic alkylation of fluorobis(phenylsulfonyl)methane (FBSM) has been realized by [Ir(COD)Cl](2)/phosphoramidite, affording enantiopure fluorobis(phenylsulfonyl)methylated compounds bearing a terminal alkene, which could be converted to monofluoro-methylated ibuprofen in just two steps without loss of the optical purity (95% ee).
متن کاملSynthesis of flinderoles B and C by a gold-catalyzed allene hydroarylation().
The recent development of new gold(I) catalysis methodologies has opened the door to new disconnections for the total synthesis of bioactive complex molecules. Below is described the application of a gold(I)-catalyzed hydroarylation of an allene with indole toward the total synthesis of flinderoles B-C, members of a new class of antimalarial bisindole alkaloids isolated from plants of the Flind...
متن کاملRuthenium-catalyzed oxidative ortho-benzoxylation of acetanilides with aromatic acids.
Substituted acetanilides reacted with aromatic acids in the presence of [{RuCl2(p-cymene)}2], AgSbF6 and (NH4)2S2O8 in ClCH2CH2Cl at 100 °C for 24 h yielding ortho-benzoxylated acetanilides in good to excellent yields in a highly regioselective manner via C-H bond activation.
متن کاملIridium-catalyzed selective α-methylation of ketones with methanol.
Iridium-catalyzed selective α-dimethylation and α-methylation of ketones or phenylacetonitriles, using methanol as the methylating agent, were achieved. In addition, three-component cross α-methyl-alkylation was successfully performed using methyl ketones with methanol and primary alcohols with long-chain alkyl groups. This method provides a very convenient direct route to α-methylated ketones,...
متن کامل