Metal-free oxidative decarbonylative coupling of aromatic aldehydes with arenes: direct access to biaryls.

نویسندگان

  • Ren-Jin Tang
  • Qing He
  • Luo Yang
چکیده

A metal-free oxidative decarbonylative coupling of aromatic aldehydes with electron-rich or electron-deficient arenes to produce biaryl compounds was developed. This novel coupling was proposed to proceed via a non-chain radical homolytic aromatic substitution (HAS) type mechanism, based on the substrate scope, ortho-regioselectivity, radical trapping experiments and DFT calculation studies. With the ready availability of aromatic aldehydes and arenes, metal-free conditions should make this coupling attractive for the biaryl synthesis.

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

منابع مشابه

Phosphine ligand triggered oxidative decarbonylative homocoupling of aromatic aldehydes: selectively generating biaryls and diarylketones.

A novel rhodium-catalyzed oxidative decarbonylative homocoupling of aromatic aldehydes to generate biaryls and diarylketones selectively and efficiently, triggered by the choice of different phosphine ligands.

متن کامل

Transition-metal-free oxidative trifluoromethylation of unsymmetrical biaryls with trifluoromethanesulfinate.

A transition-metal-free direct oxidative trifluoromethylation of unsymmetrical biaryls has been achieved by the simple combination of trifluoromethanesulfinate and phenyliodine bis(trifluoroacetate). The trifluoromethylation is selectively observed in the electron-rich arenes.

متن کامل

New catalytic transformations of carboxylic acids*

A series of metal-catalyzed processes are presented, in which carboxylic acids act as sources of either carbon nucleophiles or electrophiles, depending on the catalyst employed, the mode of activation, and the reaction conditions. A first reaction mode is the addition of carboxylic acids or amides over C–C multiple bonds, giving rise to enol esters or enamides, respectively. The challenge here ...

متن کامل

Friedel–Crafts synthesis of triarylmethanes over 3-methyl-1-sulfonic acid imidazolium tetrachloroaluminate under solvent-free conditions

Friedel–Crafts synthesis of triarylmethanes over 3-methyl-1-sulfonic acid imidazolium tetrachloroaluminate under green conditions:In this work, Friedel–Crafts (FC) alkylation of various arenes with aromatic aldehydes catalyzed by 3-methyl-1-sulfonic acid imidazoliumtetrachloroaluminate {[Msim]AlCl4}, as a green catalyst, to prepare triarylmethanes (TAMs) has been carried out. Some aromatic alde...

متن کامل

Syntheses of thiol and selenol esters by oxidative coupling reaction of aldehydes with RYYR (Y = S, Se) under metal-free conditions.

Thiol and selenol esters were synthesized by a direct oxidative coupling reaction of aldehydes with disulfides or diselenides in ethyl acetate under metal-free conditions. Among the oxidants examined, tert-butyl peroxide (TBP) was shown to give the best results. For the substrates with both electron-donating and electron-withdrawing substituents, the reaction proceeded smoothly and gave moderat...

متن کامل

ذخیره در منابع من


  با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

عنوان ژورنال:
  • Chemical communications

دوره 51 27  شماره 

صفحات  -

تاریخ انتشار 2015