Synthesis of a diboryl-N-heterocycle and its conversion to a bidentate cationic Lewis acid.

نویسندگان

  • Jeffrey M Farrell
  • Douglas W Stephan
چکیده

Sequential reaction of 2-lithio-1-methylimidazole with 9-borabicyclo[3.3.1]nonane (9-BBN) dimer and 9-Cl-9-BBN yields diboryl-N-heterocycle C4H5N2(H)(BC8H14)2 (1). Reaction of 1 with I2 results in the net substitution of chelated hydride for a singly boron-bound iodide to produce C4H5N2(I)(BC8H14)2 (2). Conversely, reaction of 1 with [Ph3C][B(C6F5)4] results in the formation of the bidentate cationic Lewis acid [(C4H5N2)(BC8H14)2][B(C6F5)4] (3). Compound 3 catalyzes the hydrogenation of N-benzylidene-tert-butylamine at room-temperature.

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

Solvent-free and one-pot Biginelli synthesis of 3,4-dihydropyrimidin-2(1H)-ones and 3,4-dihydropyrimidin-2(1H)-thiones using ionic liquid N,N-diethyl-N-sulfoethanammonium chloride {[Et3N–SO3H]Cl} as a green catalyst.

In this work, the ionic liquid triethylamine-bonded sulfonic acid {[Et3N–SO3H]Cl}, N,N-diethyl-N-sulfoethanammonium chloride was used as a green acidic homogeneous catalyst to synthesis of 3,4-dihydropyrimidin-2(1H)-ones and 3,4-dihydropyrimidin-2(1H)-thiones as two categories of heterocycles, from aldehyde, dicarbonyl compound and urea or thiourea throughout the one-pot three components cycloc...

متن کامل

Synthesis of Bis-4-hydroxycoumarins via a Multi Component Reaction Using Silica Boron-sulfuric Acid Nanoparticles (SBSANs) as an Efficient Heterogeneous Solid Acid Catalyst

The silica boron sulfuric acid nanoparticles (SBSANs) as an efficient heterogeneous solid acid catalyst with both Brønsted and Lewis acidic sites catalyzed the preparation of bis-4-hydroxycoumarin derivatives using reaction of aldehydes and 4-hydroxycoumarin under mild and solvent-free condition at room temperature. This new and efficient methodology has advantages in comparison with currently ...

متن کامل

Novel Cationic Dye Based on Naphthalimide: Part 1: Synthesis, Characterization and Evaluation of Biology Efficacy as Antimicrobial Agent

In this paper, synthesis and antimicrobial properties of cationic dye were investigated. 4-acetylamino-N-2-aminomethylpyridine-1,8-naphthalimide was reacted with 1-bromobutane as the alkylating agent and a cationic dye was obtained. The final product was purified by column chromatography method. The chemical structure of the novel cationic dye and its intermediates was chracterisized by using F...

متن کامل

N,N,N,N-Tetramethylguanidinium acetate as an efficient and reusable ionic liquid catalyst for the one-pot synthesis of dihydropyrrol-2-ones

An extremely facile and efficient procedure which has been developed for the synthesis of dihydropyrrol-2-ones. One-pot four-component reaction of amines, dialkyl acetylenedicarboxylates and formaldehyde in the presence of N,N,N,N-tetramethylguanidinium acetate [TMG][Ac] in methanol at ambient temperature provides substituted dihydropyrrol-2-ones in good to high yields. The important aspects of...

متن کامل

STUDY OF THE OPTIMUM CALCINATION TEMPERATURE FOR THE SYNTHESIS OF STRONTIUM HEXAFERRITE MAGNETIC CERAMIC NANOPOWDER BY A SOL-GEL AUTO-COMBUSTION METHOD IN THE PRESENCE OF CATIONIC SURFACTANT

In this research the sol-gel auto-combustion method was used to prepare strontium hexaferrite nanopowder. A solution of distilled water, ferric and strontium nitrates, citric acid, trimethylamine, and n-decyltrimethylammonium bromide cationic surfactant, was heated to form a viscous gel. The gel was heated and then ignited automatically. As-burnt powder was calcined at temperatures from 700 to ...

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:
  • Chemical communications

دوره 51 76  شماره 

صفحات  -

تاریخ انتشار 2015