Aerobic oxidative amination of unactivated alkenes catalyzed by palladium.

نویسندگان

  • Jodie L Brice
  • Jenna E Harang
  • Vitaliy I Timokhin
  • Natia R Anastasi
  • Shannon S Stahl
چکیده

The first examples of palladium-catalyzed oxidative amination of unactivated alkyl olefins have been identified. To be successful, these reactions must be conducted under cocatalyst-free conditions that involve direct dioxygen-coupled turnover of the palladium catalyst. The oxidative amination products of norbornene and other cyclic alkenes implicate a cis-aminopalladation mechanism.

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 oxidative amination of alkenes: improved catalyst reoxidation enables the use of alkene as the limiting reagent.

Palladium-catalyzed methods for intermolecular aerobic oxidative amination of alkenes have been identified that are compatible with the use of alkene as the limiting reagent. These procedures, which enhance the utility of this reaction with alkenes that are not commercially available, are demonstrated with substrates bearing dialkyl ether, carboxyester, epoxide, and silyl ether groups.

متن کامل

Palladium-Catalyzed Intermolecular Oxidative Amination of Alkenes with Amines, Using Molecular Oxygen as Terminal Oxidant

In this review, we summarize recent progress from our group with regard to Pd-catalyzed oxidative amination of alkenes with amines. Intermolecular oxidative amination of alkenes with secondary anilines was induced using a palladium-complex catalyst combined with molybdovanadophosphate as a co-catalyst under dioxygen, leading to allylic amines and enamines in good yields with high selectivities....

متن کامل

Aerobic intramolecular oxidative amination of alkenes catalyzed by NHC-coordinated palladium complexes.

[reaction: see text] Palladium(II) complexes bearing a single N-heterocyclic carbene ligand serve as effective catalysts for the aerobic oxidative cyclization of alkenes with pendant sulfonamides. The use of carboxylic acid cocatalysts (AcOH and PhCO(2)H) often leads to significant improvements in catalyst stability and product yield and enables catalytic turnover to be achieved with air, rathe...

متن کامل

Regioselective palladium-catalyzed intramolecular oxidative aminofluorination of unactivated alkenes.

A novel Pd-catalyzed regioselective intramolecular aminofluorination of unactivated alkenes has been developed, which is an efficient method for the synthesis of a variety of monofluoromethylated nitrogen-containing heterocycles.

متن کامل

Mechanistic studies of Wacker-type intramolecular aerobic oxidative amination of alkenes catalyzed by Pd(OAc)2/pyridine.

Wacker-type oxidative cyclization reactions have been the subject of extensive research for several decades, but few systematic mechanistic studies of these reactions have been reported. The present study features experimental and DFT computational studies of Pd(OAc)(2)/pyridine-catalyzed intramolecular aerobic oxidative amination of alkenes. The data support a stepwise catalytic mechanism that...

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:
  • Journal of the American Chemical Society

دوره 127 9  شماره 

صفحات  -

تاریخ انتشار 2005