Enantioselective Cu-Catalyzed Arylation of Secondary Phosphine Oxides with Diaryliodonium Salts toward the Synthesis of P-Chiral Phosphines

نویسندگان

  • Rodolphe Beaud
  • Robert J. Phipps
  • Matthew J. Gaunt
چکیده

Catalytic synthesis of nonracemic P-chiral phosphine derivatives remains a significant challenge. Here we report Cu-catalyzed enantioselective arylation of secondary phosphine oxides with diaryliodonium salts for the synthesis of tertiary phosphine oxides with high enantiomeric excess. The new process is demonstrated on a wide range of substrates and leads to products that are well-established P-chiral catalysts and ligands.

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

Synthesis of quaternary aryl phosphonium salts: photoredox-mediated phosphine arylation.

We report a synthesis method for the construction of quaternary aryl phoshonium salts at ambient temperature. The regiospecific reaction involves the coupling of phosphines with aryl radicals derived from diaryliodonium salts under photoredox conditions.

متن کامل

Enantioselective and Regiodivergent Copper-Catalyzed Electrophilic Arylation of Allylic Amides with Diaryliodonium Salts

A catalytic enantioselective and regiodivergent arylation of alkenes is described. Chiral copper(II)bisoxazoline complexes catalyze the addition of diaryliodonium salts to allylic amides in excellent ee. Moreover, the arylation can be controlled by the electronic nature of the diaryliodonium salt enabling the preparation of nonracemic diaryloxazines or β,β'-diaryl enamides.

متن کامل

Pd-catalyzed dynamic kinetic enantioselective arylation of silylphosphines.

Chiral phosphines are essential ligands for asymmetric transitionmetal-catalyzed transformations.1 In 1972, Knowles and co-workers reported the first practical and highly asymmetric hydrogenation using P-stereogenic phosphines,2 yet planar chiral and point chiral phosphines are the most commonly employed ligands today. P-Stereogenic phosphines are less often utilized, in part due to the lack of...

متن کامل

Rational design of novel ligands for environmentally benign cross-coupling reactions*

Transition-metal (TM) complexes of new phosphines, readily prepared by a straight forward three-step modular synthesis, were successfully employed in difficult crosscoupling reactions conducted under mild conditions (water, “open-flask”, low temperature) that aspire to meet green chemistry criteria. High yielding catalyzed by bismuth or rhodium complexes oxidative arylation of naphthoquinone ga...

متن کامل

Copper-catalyzed one-pot synthesis of unsymmetrical arylurea derivatives via tandem reaction of diaryliodonium salts with N-arylcyanamide.

An efficient "one-pot" approach to multiple substituted ureas from N-arylcyanamide and diaryliodonium salts has been presented. The two-step procedure involved the weak base-promoted chemoselective arylation of secondary amines with diaryliodonium and Cu-catalyzed nucleophilic addition of N-arylcyanamide with second diaryliodonium. The diverse unsymmetrical arylureas were obtained in up to 91% ...

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:

دوره 138  شماره 

صفحات  -

تاریخ انتشار 2016