Borane Catalyzed Selective Diazo Cross‐Coupling Towards Pyrazoles

نویسندگان

چکیده

Decomposition of donor-acceptor diazo compounds leads to the formation reactive carbene intermediates. These can undergo a wide variety transfer reactions yield synthetically useful products. Herein, we report selective borane catalyzed cyclization reaction from combination two different afford N-substituted pyrazoles. The decomposition more α-aryl α-diazoester and subsequent with vinyl diazoacetate produces N-alkylated pyrazoles in regioselective manner. Catalytic amounts tris(pentafluorophenyl)borane (10 mol%) were employed pyrazole products (36 examples) yields 59 80%. Extensive DFT studies have been undertaken interpret mechanism for this which was found go through tandem catalytic cycles, both by B(C6F5)3.

برای دانلود باید عضویت طلایی داشته باشید

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

منابع مشابه

Rhodium-catalyzed cysteine modification with diazo reagents.

A simple rhodium(II) complex catalyzes cysteine modification with diazo reagents. The reaction is marked by clean cysteine selectivity and mild reaction conditions. The resulting linkage is significantly more stable in human plasma serum, when compared to common maleimide reagents.

متن کامل

Gold-catalyzed intramolecular diazo coupling: an efficient macrocyclization towards cyclic olefins.

A gold-catalyzed intramolecular coupling of diazo compounds to produce cyclic olefins has been well established. The medium and large sized membered olefins were obtained in moderate to good yields. Notably, the Z/E selectivity of the olefins highly depended on the ring size. Furthermore, this investigation indicated that the structure of the phosphorous ligand binding to the gold centre played...

متن کامل

Mechanism of rhodium-catalyzed carbene formation from diazo compounds.

[reaction: see text] A large and normal nitrogen-15 kinetic isotope effect of 1.035 +/- 0.003 provides direct support for the proposed mechanism for the rhodium-catalyzed carbene formation from diazo compounds, which involves the fast formation of a metal-diazo complex followed by rate-limiting extrusion of N2. The large magnitude of the KIE indicates extensive C-N bond fission in the transitio...

متن کامل

A borane-bithiophene-BODIPY triad: intriguing tricolor emission and selective fluorescence response towards fluoride ions.

The structure and photophysical properties of a new triad (borane–bithiophene–BODIPY) 1 have been investigated. Triad 1 exhibits unprecedented tricolour emission when excited at the borane centred high energy absorption band and also acts as a selective fluorescent and colorimetric sensor for fluoride ions with ratiometric response. The experimental results are supported by computational studies.

متن کامل

Molybdenum Catalyzed Ammonia Borane Dehydrogenation: Oxidation State Specific Mechanisms

Though numerous catalysts for the dehydrogenation of ammonia borane (AB) are known, those that release >2 equiv of H2 are uncommon. Herein, we report the synthesis of Mo complexes supported by a para-terphenyl diphosphine ligand, 1, displaying metal-arene interactions. Both a Mo(0) N2 complex, 5, and a Mo(II) bis(acetonitrile) complex, 4, exhibit high levels of AB dehydrogenation, releasing ove...

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

ژورنال

عنوان ژورنال: Advanced Synthesis & Catalysis

سال: 2021

ISSN: ['1615-4169', '1615-4150']

DOI: https://doi.org/10.1002/adsc.202101312