Palladium-Catalyzed Amination of Aryl Chlorides and Bromides with Ammonium Salts

نویسندگان

  • Rebecca A. Green
  • John F. Hartwig
چکیده

We report the palladium-catalyzed coupling of aryl halides with ammonia and gaseous amines as their ammonium salts. The coupling of aryl chlorides and ortho-substituted aryl bromides with ammonium sulfate forms anilines with higher selectivity for the primary arylamine over the diarylamine than couplings with ammonia in dioxane. The resting state for the reactions of aryl chlorides is different from the resting state for the reactions of aryl bromides, and this change in resting states is proposed to account for a difference in selectivities for reactions of the two haloarenes.

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

Aqueous hydroxide as a base for palladium-catalyzed amination of aryl chlorides and bromides.

The amination of aryl halides in the presence of inexpensive and air-stable alkali metal hydroxide bases and Pd[P(t-Bu)3]2 as catalyst gave arylamines in high yields. The reactions were conducted with a catalytic amount of cetyltrimethylammonium bromide as phase-transfer agent and either aqueous hydroxide or solid hydroxide in the presence of water. This combination of alkali metal hydroxide ba...

متن کامل

Efficient copper-catalyzed amination of aryl halides with amines and N H heterocycles using rac-BINOL as ligand

A highly efficient copper-catalyzed system using commercially available racemic 1,1′-binaphthyl-2,2′-diol (rac-BINOL) as the ligand was eveloped for amination of aryl halides and heteroaryl halides with alkyl amines and N H heterocycles. Good to high yields were obtained for aryl romides and heteroaryl chlorides. The commercially available rac-BINOL ligand with excellent stability and high effi...

متن کامل

[2.2]Paracyclophane-based monophosphine ligand for palladium-catalyzed cross-coupling reactions of aryl chlorides.

A new [2.2]paracyclophane-based electron-rich and sterically bulky monophosphine ligand has been synthesized by an efficient and straightforward method. When combined with palladium, this ligand shows excellent performance in the Buchwald-Hartwig amination and Suzuki-Miyaura coupling reactions of various aryl chlorides. In both types of reactions, ortho-substituted, deactivated aryl chlorides a...

متن کامل

Palladium-Catalyzed α-Arylation of Aryl Acetic Acid Derivatives via Dienolate Intermediates with Aryl Chlorides and Bromides

To date, examples of α-arylation of carboxylic acids remain scarce. Using a deprotonative cross-coupling process (DCCP), a method for palladium-catalyzed γ-arylation of aryl acetic acids with aryl halides has been developed. This protocol is applicable to a wide range of aryl bromides and chlorides. A procedure for the palladium-catalyzed α-arylation of styryl acetic acids is also described.

متن کامل

Palladium-catalyzed conversion of aryl and vinyl triflates to bromides and chlorides.

The palladium-catalyzed conversion of aryl and vinyl triflates to aryl and vinyl halides (bromides and chlorides) has been developed using dialkylbiaryl phosphine ligands. A variety of aryl, heteroaryl, and vinyl halides can be prepared via this method in good to excellent yields.

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 16  شماره 

صفحات  -

تاریخ انتشار 2014