Deoxycyanamidation of Alcohols with N-Cyano-N-phenyl-p-methylbenzenesulfonamide (NCTS).

نویسندگان

  • James N Ayres
  • Matthew W Ashford
  • Yannick Stöckl
  • Vassili Prudhomme
  • Kenneth B Ling
  • James A Platts
  • Louis C Morrill
چکیده

The first one-pot deoxycyanamidation of alcohols has been developed using N-cyano-N-phenyl-p-methylbenzenesulfonamide (NCTS) as both a sulfonyl transfer reagent and a cyanamide source, accessing a diverse range of tertiary cyanamides in excellent isolated yields. This approach exploits the underdeveloped desulfonylative (N-S bond cleavage) reactivity pathway of NCTS, which is more commonly employed for electrophilic C- and N-cyanation processes.

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

Functionalization of Styrenes by Copper-Catalyzed Borylation/ ortho-Cyanation and Silver-Catalyzed Annulation Processes.

An efficient two-step method for the assembly of indanone derivatives starting from a simple vinyl arene has been developed. The sequence first involves addition of bis(pinacolato)diboron (B2 pin2 ) and N-cyano-N-phenyl-p-methylbenzenesulfonamide (NCTS) to a broad range of styrenes by utilizing IMesCuCl as catalyst. This step simultaneously accomplishes hydroboration of the alkene and ortho cya...

متن کامل

Rhodium(III)-Catalyzed Selective C¢H Cyanation of Indolines and Indoles with an Easily Accessible Cyano Source

The rhodium-catalyzed selective cyanation of C¢H bonds of indolines and indoles with Ncyano-N-phenyl-para-methylbenzenesulfonamide is described. This protocol offers a facile access to C-7 cyanated indolines and C-2 cyanated indoles with high site selectivity and excellent functional group tolerance.

متن کامل

Selective conversion of alcohols and phenols to tetrahydropyranyl ethers catalyzed with N-chlorosaccharin under mild and solvent-free conditions

An efficient method is described for the mild and rapid tetrahydropyranylation of alcohols and phenols using a catalytic amount of N-chlorosaccharin (1 mol %) and 3, 4-dihydro-2H-pyran under solvent-free condition at room temperature. Benzylic alcohols and phenols containing electron withdrawing or donating groups in various positions of phenyl ring, cinamyl alcohol, primary, ...

متن کامل

Selective conversion of alcohols and phenols to tetrahydropyranyl ethers catalyzed with N-chlorosaccharin under mild and solvent-free conditions

An efficient method is described for the mild and rapid tetrahydropyranylation of alcohols and phenols using a catalytic amount of N-chlorosaccharin (1 mol %) and 3, 4-dihydro-2H-pyran under solvent-free condition at room temperature. Benzylic alcohols and phenols containing electron withdrawing or donating groups in various positions of phenyl ring, cinamyl alcohol, primary, ...

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:
  • Organic letters

دوره 19 14  شماره 

صفحات  -

تاریخ انتشار 2017