Direct synthesis of anilines and nitrosobenzenes from phenols.

نویسندگان

  • A H St Amant
  • C P Frazier
  • B Newmeyer
  • K R Fruehauf
  • J Read de Alaniz
چکیده

A one-pot synthesis of anilines and nitrosobenzenes from phenols has been developed using an ipso-oxidative aromatic substitution ((i)SOAr) process. The products are obtained in good yields under mild and metal-free conditions. The leaving group effect on reactions that proceed through mixed quionone monoketals has also been investigated and a predictive model has been established.

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

Palladium-catalyzed reductive coupling of phenols with anilines and amines: efficient conversion of phenolic lignin model monomers and analogues to cyclohexylamines† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c5sc00941c

Phenols, being readily available from naturally abundant lignins, are important future feedstocks for the renewable production of fuels, chemicals, and energy. Herein, a highly efficient Pd-catalyzed direct coupling of phenolic lignin model monomers and analogues with anilines to give cyclohexylamines using cheap and safe sodium formate as hydrogen donor is described. A variety of secondary and...

متن کامل

QSAR analysis of soil sorption coefficients for polar organic chemicals: substituted anilines and phenols.

Based on descriptors of n-octanol/water partition coefficients (logKow), molecular connectivity indices, and quantum chemical parameters, several QSAR models were built to estimate the soil sorption coefficients (logKoc) of substituted anilines and phenols. Results showed that descriptor logKow plus molecular quantum chemical parameters gave poor regression models. Further study was performed t...

متن کامل

Formal Direct Cross-Coupling of Phenols with Amines.

The transition-metal-catalyzed amination of aryl halides has been the most powerful method for the formation of aryl amines over the past decades. Phenols are regarded as ideal alternatives to aryl halides as coupling partners in cross-couplings. An efficient palladium-catalyzed formal cross-coupling of phenols with various amines and anilines has now been developed. A variety of substituted ph...

متن کامل

Regioselective Iodination of Chlorinated Aromatic Compounds Using Silver Salts.

The iodination of chlorinated aromatic compounds using Ag(2)SO(4)/I(2), AgSbF(6)/I(2), AgBF(4)/I(2) and AgPF(6)/I(2) offers access to iodoarenes that are valuable intermediates in organic synthesis. Specifically, iodination of phenols, anisoles and anilines with a 3,5-dichloro substitution pattern preferentially yielded the ortho, para and para iodinated product, respectively. In the case of ch...

متن کامل

3-Hydroxypropylammonium acetate (HPAA) ionic liquid: An effective acidic media in efficient conversion of anilines into aryl isocyanates

A simple and mild procedure for the conversion of anilines into aryl isocyanates is described using the 3-hydroxypropylammonium acetate (HPAA) ionic liquid as a novel and efficient media has been explored in the synthesis of aryl isocyanates from the reaction of substituted urea with sodium nitrite in a water immiscible solvent. This ionic liquid can be easily recovered and reused for many time...

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 & biomolecular chemistry

دوره 14 24  شماره 

صفحات  -

تاریخ انتشار 2016